21085-72-3 Archives - Bromides-buliding-blocks

Tian, Jiameng’s team published research in Synlett in 2020 | CAS: 21085-72-3

(2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(cas: 21085-72-3) may be used for the synthesis of HMR1098-S-Glucuronide Methyl Ester, a new K-ATP-blocking agent being developed as a drug for prevention of sudden cardiac death.Product Details of 21085-72-3

《Practical Synthesis of the Fluorogenic Enzyme Substrate 4-Methylumbelliferyl α-L-Idopyranosiduronic Acid》 was written by Tian, Jiameng; Ouyang, Wenliang; He, Yanling; Ning, Qianqian; Bai, Jiang; Ding, Haixin; Xiao, Qiang. Product Details of 21085-72-3 And the article was included in Synlett in 2020. The article conveys some information:

A practical and concise synthesis of 4-methylumbelliferyl α-L-idopyranosiduronic acid, a fluorogenic enzyme substrate diagnostic for α-L-iduronidase, was accomplished. It features successive radical bromination and radical reduction of easily accessible Me 4-methylumbelliferyl-2,3,4-tri-O-acetyl-β- D-glucouronate in four steps with 28% overall yield. The experimental part of the paper was very detailed, including the reaction process of (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(cas: 21085-72-3Product Details of 21085-72-3)

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Li, Ming’s team published research in Organic Letters in 2020 | CAS: 21085-72-3

《Visible-Light-Induced Pd-Catalyzed Radical Strategy for Constructing C-Vinyl Glycosides》 was published in Organic Letters in 2020. These research results belong to Li, Ming; Qiu, Yi-Feng; Wang, Cui-Tian; Li, Xue-Song; Wei, Wan-Xu; Wang, Yu-Zhao; Bao, Qiao-Fei; Ding, Ya-Nan; Shi, Wei-Yu; Liang, Yong-Min. COA of Formula: C13H17BrO9 The article mentions the following:

A novel visible-light-induced palladium-catalyzed Heck reaction for bromine sugars and aryl olefins with high regio- and stereochem. selectivity for the preparation of C-glycosyl styrene is described. This reaction takes place in one step at room temperature by using a simple and readily available starting material. This protocol can be scaled up to a wide range of glycosyl bromide donors and aryl olefin substrates. Mechanistic studies indicate that a radical addition pathway is involved. The results came from multiple reactions, including the reaction of (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(cas: 21085-72-3COA of Formula: C13H17BrO9)

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Xia, Liwen’s team published research in ACS Catalysis in 2021 | CAS: 21085-72-3

《Photoredox-Catalyzed Stereoselective Synthesis of C-Nucleoside Analogs from Glycosyl Bromides and Hetero-arenes》 was written by Xia, Liwen; Fan, Wenjing; Yuan, Xiang-Ai; Yu, Shouyun. HPLC of Formula: 21085-72-3 And the article was included in ACS Catalysis in 2021. The article conveys some information:

C-nucleosides, analogs of nucleosides by replacing a C-N glycosidic bond with a C-C bond, are potential anticancer or antiviral agents. Synthesis of C-nucleoside analogs, e.g. I, enabled by photoredox-catalyzed radical coupling of glycosyl bromides with non-functionalized hetero-arenes has been described. This strategy features readily available starting materials, mild conditions, good functional group tolerance, and site- and stereoselectivities (α-configuration). A variety of monosaccharides (D-lyxose, D-ribose, L-arabinose, D-glucose, D-mannose, D-glucuronide, and D-fucose), disaccharides (lactose, melibiose, and maltose), and polysaccharide can couple with a series of non-functionalized hetero-arenes, such as purine, benzothiazole, thiazolo-pyridine, benzoxazole, benzimidazole, imidazopyridine, and phenanthridine. Biol. important mols., such as theophylline, famciclovir, ribofuranoside, and adenine, can be glycosylated directly through a C-C bond using this method. Site- and stereoselectivities can be rationalized and predicted by DFT calculations In the experimental materials used by the author, we found (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(cas: 21085-72-3HPLC of Formula: 21085-72-3)

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Liu, Jun’s team published research in Chemical Science in 2021 | CAS: 21085-72-3

《Ultrasensitive small molecule fluorogenic probe for human heparanase》 was written by Liu, Jun; Schleyer, Kelton A.; Bryan, Tyrel L.; Xie, Changjian; Seabra, Gustavo; Xu, Yongmei; Kafle, Arjun; Cui, Chao; Wang, Ying; Yin, Kunlun; Fetrow, Benjamin; Henderson, Paul K. P.; Fatland, Peter Z.; Liu, Jian; Li, Chenglong; Guo, Hua; Cui, Lina. Name: (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetateThis research focused onultrasensitive fluorogenic probe human heparanase. The article conveys some information:

Heparanase (HPA) is a critical enzyme involved in the remodeling of the extracellular matrix (ECM), and its elevated expression has been linked with diseases such as various types of cancer and inflammation. The detection of heparanase enzymic activity holds tremendous value in the study of the cellular microenvironment, and search of mol. therapeutics targeting heparanase, however, no structurally defined probes are available for the detection of heparanase activity. Here we present the development of the first ultrasensitive fluorogenic small-mol. probe for heparanase enzymic activity via tuning the electronic effect of the substrate. The probe exhibits a 756-fold fluorescence turn-on response in the presence of human heparanase, allowing one-step detection of heparanase activity in real-time with a picomolar detection limit. The high sensitivity and robustness of the probe are exemplified in a high-throughput screening assay for heparanase inhibitors. In the experiment, the researchers used (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(cas: 21085-72-3Name: (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate)

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Li, Cai-Yi’s team published research in Organic Letters in 2021 | CAS: 21085-72-3

Li, Cai-Yi; Ma, Yue; Lei, Zhi-Wei; Hu, Xiang-Guo published their research in Organic Letters in 2021. The article was titled 《Glycosyl-Radical-Based Synthesis of C-Alkyl Glycosides via Photo-mediated Defluorinative gem-Difluoro-allylation》.COA of Formula: C13H17BrO9 The article contains the following contents:

We have developed a stereoselective, glycosyl radical-based method for the synthesis of C-alkyl glycosides via a photo-mediated defluorinative gem-difluoroallylation reaction. We demonstrate for the first time that glycosyl radicals, generated from glycosyl bromides, can readily participate in a photo-mediated radical polar crossover process, affording a diverse array of gem-difluoro-alkene containing C-glycosides. Notable features of this method include scalability, mild conditions, broad substrate scope, and suitability for the late-stage modification of complex mols. In the experiment, the researchers used many compounds, for example, (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(cas: 21085-72-3COA of Formula: C13H17BrO9)

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Xia, Liwen’s team published research in Organic Letters in 2022 | CAS: 21085-72-3

Xia, Liwen; Jin, Maolu; Jiao, Yi; Yu, Shouyun published an article in 2022. The article was titled 《Synthesis of C-Alkynyl Glycosides by Photoredox-Catalyzed Reductive Coupling of Alkynyl Bromides with Glycosyl Bromides》, and you may find the article in Organic Letters.Quality Control of (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate The information in the text is summarized as follows:

A general, convenient, and highly α stereoselective approach to access C-alkynyl glycosides via the photoredox-catalyzed reductive coupling of alkynyl bromides and glycoside bromides has been developed. Cheap and small-load eosin Y is used as the photocatalyst, and organic base N,N-diisopropylethylamine serves as the reducing reagent. This strategy features readily available starting materials, diverse substrates, mild conditions, and high α stereoselectivity. Moreover, a glycoconjugate peptide could also be achieved using this strategy. After reading the article, we found that the author used (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(cas: 21085-72-3Quality Control of (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate)

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Lin, Miao’s team published research in Analytica Chimica Acta in 2020 | CAS: 21085-72-3

《Global profiling and identification of bile acids by multi-dimensional data mining to reveal a way of eliminating abnormal bile acids》 was written by Lin, Miao; Chen, Xiong; Wang, Zhe; Wang, Dongmei; Zhang, Jin-Lan. Recommanded Product: 21085-72-3 And the article was included in Analytica Chimica Acta in 2020. The article conveys some information:

Bile acids (BAs), as crucial endogenous metabolites, are closely related to cholestasis, metabolic disorders, and cancer. To better understand their function and disease pathogenesis, global profiling of BAs is necessary. Here, multidimensional data mining was developed for the discovery and identification of potentially unknown BAs in cholestasis rats. Based on an inhouse theor. BA database and using a newly established liquid chromatog.-tandem high-resolution mass spectrometry (LC-HRMS/MS) method, four-dimensional (4D) data including the retention times (RT), abundances, HRMS, and HRMS/MS spectra were acquired and elucidated. And 491 BAs were totally profiled. Then, the relations between RT with different conjugation types, different positions and configurations of hydroxyl/ketone groups as well as fragmentation rules of hydroxyl, ortho-hydroxyl, ketone, and conjugated groups of BAs were summarized to assist BA identification for the first time. Finally, 292 BAs were assigned with mol. formulas, 201 of which were putatively identified by integrating the 4D data, applying structure-driven relative retention time rules, and a comparison with synthetic BAs. The estimated concentrations of 201 BAs, including 93 reported and 108 newly identified BAs, were quantified by using surrogate standards with similar structure. Among 201 BAs, 38 BAs were detected in both humans and rats for the first time. The authors′ strategy has expanded the scope of BAs and provides a way to identify a class of metabolites. Compared to normal rats, the significantly increased sulfated and glucuronide conjugated BAs in urine and feces from exptl. cholestatic rats may reveal a way to diagnose intrahepatic cholestasis. In the experiment, the researchers used many compounds, for example, (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(cas: 21085-72-3Recommanded Product: 21085-72-3)

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Park, Suho’s team published research in Bioconjugate Chemistry in 2019 | CAS: 21085-72-3

In 2019,Bioconjugate Chemistry included an article by Park, Suho; Kim, Sun Young; Cho, Jongun; Jung, Doohwan; Seo, Donghoon; Lee, Jaeho; Lee, Sangkwang; Yun, Sanghyeon; Lee, Hyangsook; Park, Okku; Seo, Beomseok; Woo, Sung Ho; Park, Tae Kyo. SDS of cas: 21085-72-3. The article was titled 《Aryl Sulfate is a Useful Motif for Conjugating and Releasing Phenolic Molecules: Sulfur Fluorine Exchange Click Chemistry Enables Discovery of Ortho-Hydroxy-Protected Aryl Sulfate Linker》. The information in the text is summarized as follows:

A new self-immolative linker motif, Ortho Hydroxy-Protected Aryl Sulfate (OHPAS), was devised, and OHPAS-containing antibody drug conjugates (ADC) were tested in vitro and in vivo. Conveniently synthesized using Sulfur Fluorine Exchange (SuFEx) chem., it is based structurally on diaryl sulfate, with one aryl acting as a payload and the other as a self-immolative sulfate unit having a latent phenol function at the ortho position. The chem. stable OHPAS linker was stable in plasma samples from 5 different species, yet it can release the payload mol. smoothly upon chem. or biol. triggering. The payload release proceeds via intramol. cyclization, producing a cyclic sulfate coproduct that eventually hydrolyzes to a catechol monosulfate. A set of OHPAS-containing ADCs based on Trastuzumab were prepared with a drug to antibody ratio of ∼2, and were shown to be cytotoxic in 5 different cancer cell lines in vitro and dose-dependently inhibited tumor growth in a NCI-N87 mouse xenograft model. We conclude that OHPAS conjugates will be of considerable use for delivering phenol-containing payloads to tissues targeted for medical intervention. The experimental process involved the reaction of (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(cas: 21085-72-3SDS of cas: 21085-72-3)

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Sharipova, Radmila R.’s team published research in MedChemComm in 2019 | CAS: 21085-72-3

In 2019,MedChemComm included an article by Sharipova, Radmila R.; Belenok, Mayya G.; Garifullin, Bulat F.; Sapunova, Anastasiya S.; Voloshina, Alexandra D.; Andreeva, Olga V.; Strobykina, Irina Yu.; Skvortsova, Polina V.; Zuev, Yuriy F.; Kataev, Vladimir E.. Recommanded Product: (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate. The article was titled 《Synthesis and anti-cancer activities of glycosides and glycoconjugates of diterpenoid isosteviol》. The information in the text is summarized as follows:

A series of glycosides and glycoconjugates of diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) with various monosaccharide residues were synthesized and their cytotoxicity against some human cancer and normal cell lines was assayed. Most of the synthesized compounds demonstrated moderate to significant cytotoxicity against human cancer cell lines M-HeLa and MCF-7. Three lead compounds exhibited selective cytotoxic activities against M-HeLa (IC50 = 10.0-15.1μM) that were three times better than the cytotoxicity of the anti-cancer drug Tamoxifen (IC50 = 28.0μM). Moreover, the lead compounds were not cytotoxic with respect to the normal human cell line Chang liver (IC50 > 100μM), whereas Tamoxifen inhibited the viability of normal human Chang liver cells with an IC50 value of 46.0μM. It was determined that the cytotoxicity of the lead compounds was due to induction of apoptosis proceeding along the mitochondrial pathway. The cytotoxic activity of the synthesized compounds substantially depended on the nature of the monosaccharide residue and its position, i.e., whether the monosaccharide residue was attached directly to the isosteviol skeleton or was moved away from it by means of a polymethylene linker. After reading the article, we found that the author used (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(cas: 21085-72-3Recommanded Product: (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate)

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Chuprakov, Stepan’s team published research in Bioconjugate Chemistry in 2021 | CAS: 21085-72-3

Application of 21085-72-3In 2021 ,《Tandem-Cleavage Linkers Improve the In Vivo Stability and Tolerability of Antibody-Drug Conjugates》 appeared in Bioconjugate Chemistry. The author of the article were Chuprakov, Stepan; Ogunkoya, Ayodele O.; Barfield, Robyn M.; Bauzon, Maxine; Hickle, Colin; Kim, Yun Cheol; Yeo, Dominick; Zhang, Fangjiu; Rabuka, David; Drake, Penelope M.. The article conveys some information:

Although peptide motifs represent the majority of cleavable linkers used in clin.-stage antibody-drug conjugates (ADCs), the sequences are often sensitive to cleavage by extracellular enzymes, such as elastase, which leads to systemic release of the cytotoxic payload. This action reduces the therapeutic index by causing off-target toxicities that can be dose-limiting. For example, a common side-effect of ADCs made using peptide-cleavable linkers is myelosuppression, including neutropenia. Only a few reports describe methods for optimizing peptide linkers to maintain efficient and potent tumor payload delivery while enhancing circulating stability. Herein, the authors address these critical limitations through the development of a tandem-cleavage linker strategy, where two sequential enzymic cleavage events mediate payload release. The authors prepared dipeptides that are protected from degradation in the circulation by a sterically encumbering glucuronide moiety. Upon ADC internalization and lysosomal degradation, the monosaccharide is removed and the exposed dipeptide is degraded, which liberates the attached payload inside the target cell. The authors used CD79b-targeted monomethyl auristatin E (MMAE) conjugates as the model system and compared the stability, efficacy, and tolerability of ADCs made with tandem-cleavage linkers to ADCs made using standard technol. with the vedotin linker. The results, where rat studies showed dramatically improved tolerability in the hematopoietic compartment, highlight the role that linker stability plays in efficacy and tolerability and also offer a means of improving an ADC’s therapeutic index for improved patient outcomes. The experimental part of the paper was very detailed, including the reaction process of (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(cas: 21085-72-3Application of 21085-72-3)

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary