Tag: 400-500

An improved preparation of (S)-N-(Boc)-cyclohexylalaninal. The Moffat-Swern oxidation of α-amino alcohols was written by Krysan, D. J.;Haight, A. R.;Lallaman, J. E.;Langridge, D. C.;Menzia, J. A.;Narayanan, B. A.;Pariza, R. J.;Reno, D. S.;Rockway, T. W.. And the article was included in Organic Preparations and Procedures International in 1993.Formula: C23H26BrP This article mentions the following:

Moffat-Swern oxidation of protected alc. (S)-BocNHCH(CH₂R)CH₂OH (I; Boc = Me₃CO₂C; R = cyclohexyl) with DMSO/(COCl)₂/EtN(CHMe₂)₂ or DMSO/pyridine-SO₃/Et₃N gave the title compound (S)-BocNHCH(CH₂R)CHO (II) in >95% enantiomeric excess. The chem. efficiency of this oxidation os demonstrated in the 2-step conversion of I to (S,Z)-BocNHCH(CH₂R)CH:CHCH₂CHMe₂ in 60% yield via subsequent olefination of intermediate II with Ph₂P⁺CH₂CH₂CHMe₂ Br^–. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Formula: C23H26BrP).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Formula: C23H26BrP

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of cytotoxic novel 9,11-secosterol analogs: Structure/activity studies was written by Kongkathip, Boonsong;Hasakunpaisarn, Anuch;Boonananwong, Suthinee;Kongkathip, Ngampong. And the article was included in Steroids in 2010.Product Details of 28322-40-9 This article mentions the following:

In an effort to determine the pharmaceutical utility and the structural requirements for activity against tumor cell lines, 30 novel 9,11-secosterol analogs with different side chains and degrees of oxidation at C-9, e.g. I, were synthesized starting from hecogenin. Evaluation of the synthesized compounds for cytotoxicity against KB, HeLa and MCF-7 cell lines revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biol. activity, the existence of a ketone functional at C-9 is also crucial for anticancer activity whereas hydroxyl/ketone function at C-22 on the side chain did not increase cytotoxicity. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Product Details of 28322-40-9).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Product Details of 28322-40-9

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Analytical chemistry of the platinum metals. VIII. Application of phosphonium and arsonium salts to the gravimetric determination of osmium was written by Neeb, R.. And the article was included in Fresenius’ Zeitschrift fuer Analytische Chemie in 1960.Electric Literature of C23H26BrP This article mentions the following:

Solubility determinations are reported of halo-osmates of substituted phosphonium and arsonium compounds, and several are investigated for determining Os. Those recommended are tetraphenylarsonium chloride and benzyltriphenylphosphonium chloride in HCl solution, and tetraphenylarsonium and tetraphenylphosphonium chlorides in HBr solution In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Electric Literature of C23H26BrP).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon–bromine bond is electrophilic in nature. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Electric Literature of C23H26BrP

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Reaction of phosphoranes with formate esters. New method for synthesis of vinyl ethers was written by Subramanyam, Vinayakam;Silver, Eileen H.;Soloway, Albert H.. And the article was included in Journal of Organic Chemistry in 1976.Category: bromides-buliding-blocks This article mentions the following:

A reinvestigation of the Wittig reaction of phosphoranes with formate esters was undertaken with the purpose of developing a new method for synthesis of substituted vinyl ethers. Stabilized, partially stabilized, and reactive phosphoranes derived from (carbethoxymethyl)-, benzyl-, (3-methylbutyl)-, and (methoxymethyl)phosphonium halides were allowed to react with ethyl formate and vinyl ethers were isolated in the first three cases. Vinylidine diethers could not be prepared by this method. Thus, Ph3P:CHR (R = CO2Et, Ph, CH2CHMe2) reacted with HCO2Et to give the resp. EtOCH:CHR. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Category: bromides-buliding-blocks).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Development of novel Gemini-cholesterol analogues for retinoid-related orphan receptors was written by Gomez-Bouzo, Uxia;Fall, Alioune;Osz, Judit;Fall, Yagamare;Rochel, Natacha;Santalla, Hugo. And the article was included in Organic Chemistry Frontiers in 2022.Related Products of 28322-40-9 This article mentions the following:

Retinoic-acid-related Orphan Receptors (RORs) regulate the maintenance of the circadian rhythm and immune response among others and are involved in increasing numbers of pathologies including autoimmune diseases, cancer and neurol. disorders leading to huge interest in the development of ROR ligands. Here, the synthesis of six novel Gemini cholesterol analogs such as I and the binding mode of I to RORγ was described. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Related Products of 28322-40-9).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Related Products of 28322-40-9

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Side chain methyl analogs of Δ⁸-THC was written by Huffman, John W.;Lainton, Julia A. H.;Banner, W. Kenneth;Duncan, Sammy G. Jr.;Jordan, Robert D.;Yu, Shu;Dai, Cong;Martin, Billy R.;Wiley, Jenny L.;Compton, David R.. And the article was included in Tetrahedron in 1997.Safety of Isopentyltriphenylphosphonium bromide This article mentions the following:

The synthesis of both side chain epimers of 1′- (I; R = CHMeBu) 2′- (I; R = CH₂CHMePr) and 3′-Me- [I; R = (CH₂)₂CHMeEt] and 4′-methyl-Δ⁸-tetrahydrocannabinol [I; R = (CH₂)₃CHMe₂] was carried out. The synthetic approach entailed the acid catalyzed condensation of the appropriate substituted resorcinol with menthadienol to provide the analog of Δ⁸-THC [I; R = (CH₂)₄Me]. Both isomers of 1′-Me- (I; R = CHMeBu) and 2′-Me-Δ⁸-THC (I; R = CH₂CHMePr) were more potent than Δ⁸-THC , both in vitro and in vivo. The 3′-Me isomers (I; R = CH₂CH₂CHMeEt) were approx. equal in potency to Δ⁸-THC, and 4′-methyl-Δ⁸-THC was less potent. There was relatively little difference in potency between the epimers of I (R = CHMeBu, CH₂CHMePr, CH₂CH₂CHMeE). In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Safety of Isopentyltriphenylphosphonium bromide).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Safety of Isopentyltriphenylphosphonium bromide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

New syntheses of 1α,25-dihydroxycholesterol was written by Fuerst, Andor;Labler, Ludvik;Meier, Werner. And the article was included in Helvetica Chimica Acta in 1982.Computed Properties of C23H26BrP This article mentions the following:

1α,25-Dihydroxycholesterol was prepared via 5 convergent syntheses by combining C₂₁– or C₂₂-steroids with C₄– or C₅-side-chain building blocks. Thus, pregnene I (R = tetrahydro-2-pyranyl, R¹ = CH₂O₃SC₆H₄Me-H) was combined with the dioxolane II, PhSO₂CH₂CH₂CMe₂OR² (R² = tetrahydro-2-pyranyl) and HCCCMe₂OR² and I (R = Ac, R¹ = CHO) was combined with Ph₃P:CHCH₂CMe₂OH. Also, pregnenone III was condensed with phosphorane IV. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Computed Properties of C23H26BrP).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Computed Properties of C23H26BrP

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

A facile approach for the total synthesis of neurotrophic diyne tetraol petrosiol A and petrosiol E was written by Gangadhar, Pamarthi;Sathish Reddy, A.;Srihari, Pabbaraja. And the article was included in Tetrahedron in 2016.Synthetic Route of C23H26BrP This article mentions the following:

The first total synthesis of neurotrophic diacetylenic tetraol, petrosiol A (I) and stereoselective total synthesis of petrosiol E (II) was accomplished. The total synthesis involves Cadiot-Chodkiewicz coupling reaction as the key step for petrosiol A. The diastereo-rich chiral alc. (third chiral center) was synthesized from CBS mediated stereoselective ketone reduction reaction for petrosiol E. Of the three chiral centers, the two chiral centers are originated from (+)-di-Et L-tartrate and the third chiral center was generated by an addition reaction of lithium trimethylsilylacetylide leading to two diastereomers which were used for the synthesis of both the natural products and their diastereomer C6-epi-petrosiol A and C6-epi-petrosiol E, resp. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Synthetic Route of C23H26BrP).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Synthetic Route of C23H26BrP

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Diastereoselectivity in the osmium-catalyzed dihydroxylation of allylic amides and carbamates was written by Krysan, Damian J.;Rockway, Todd W.;Haight, Anthony R.. And the article was included in Tetrahedron: Asymmetry in 1994.Reference of 28322-40-9 This article mentions the following:

The stereochem. of the osmium-catalyzed dihydroxylation of chiral allylic amides and carbamates I (R = BOC, PhCH₂O₂C, EtO₂C, Ac, Cl₃CO, i-BuCO, R¹ = R² = H, R³ = i-Bu; R = BOC, R¹ = R³ = H, R² = i-Bu; R¹-R³ = H, R¹ = Me, R² = R³ = H) has been studied. The diastereoselectivity depended on the solvent, the N protecting group, and the geometry and substitution pattern of the olefin substrate. In contrast to the erythro selectivity observed with allylic alcs., osmylations of I were threo selective to give threo-II (same R-R³) . Stoichiometric osmylations were consistently more selective than the corresponding catalytic reactions. Control experiments suggest this is due to the presence of a second catalytic cycle based upon an osmium glycolate catalyst which accumulates as the reaction proceeds to completion. Double diastereoselective dihydroxylations of allylic carbamates were also briefly examined In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Reference of 28322-40-9).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Reference of 28322-40-9

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Stereochemical effects in cyclopropane ring openings: biomimetic ring openings of all isomers of 22,23-methylenecholesterol acetate was written by Zimmerman, Mary P.;Li, Hui Ting;Duax, William L.;Weeks, Charles M.;Djerassi, Carl. And the article was included in Journal of the American Chemical Society in 1984.Name: Isopentyltriphenylphosphonium bromide This article mentions the following:

By using the unique stereochem. of the side chain in cholesterol, the dynamic influence of proximate chiral centers on the acid-promoted isomerizations of cyclopropanes is defined. Unexpectedly, when the cyclopropane is placed in the 22,23 position, either a backbone rearrangement is induced or unanticipated side-chain olefins arise, each dependent on the stereochem. of the cyclopropane starting material. The synthesis and stereochem. assignments of the 4 possible 22,23-methylenecholesterol acetates I are reported as well as the effect of stereochem. on the acid-promoted isomerization of these compounds [22R,23R]-I and [22S,23S]-I under the conditions of ring opening yield unexpected backbone rearrangement products, i.e., acetoxydimethylnorcholestadienes II, which can also be obtained from rearrangements of methylcholestadienol acetates III and IV. The stereochem. criteria governing the course of these isomerizations are discussed. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Name: Isopentyltriphenylphosphonium bromide).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon–bromine bond is electrophilic in nature. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Name: Isopentyltriphenylphosphonium bromide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary