51231-24-4

Usage

Uses

Used in Biosynthetic Studies:
(20S)-6-METHOXY-20-(P-TOLUENESULFONOXY-METHYL)-3B,5-CYCLO-5A-PREGNANE is used as an intermediate in the biosynthetic studies of cholic acids and vitamin D3 derivatives. Its unique structure allows for the exploration of new pathways and mechanisms in the synthesis of these important compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (20S)-6-METHOXY-20-(P-TOLUENESULFONOXY-METHYL)-3B,5-CYCLO-5A-PREGNANE is used as a key building block for the development of new drugs, particularly those targeting steroid-related conditions. Its unique chemical properties make it a valuable asset in the design and synthesis of novel therapeutic agents.
Used in Chemical Research:
(20S)-6-METHOXY-20-(P-TOLUENESULFONOXY-METHYL)-3B,5-CYCLO-5A-PREGNANE is also used in chemical research as a model compound for studying the properties and reactivity of tosylated steroids. This helps researchers gain a deeper understanding of the structural and functional aspects of these compounds, which can be applied to the development of new materials and technologies.

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 25819-77-6 6β-Methoxy-3α,5-cyclo-23,24-dinor-5α-cholan-22-al 
• 51231-23-3 3α,5-cyclo-22-hydroxy-5α-23,24-bisnorcholan-6β-ol 6-methyl ether 
• 91228-89-6 (20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carboxylic acid 
• 53603-94-4 stigmasterol methyl ether 
• 32345-19-0 24-ethylcholesta-5,22-dien-3β-ol 
• 267641-89-4 (1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-6-((E)-(R)-4-Ethyl-1,5-dimethyl-hex-2-enyl)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene 
• 83-48-7 Stigmasterol 
• 53139-42-7 stigmasteryl tosylate 
• 25819-77-6 (20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde 
• 139894-63-6 22,23-dihydrostigmasteryl methyl ether 

Downstream Products

• 69081-91-0 6β-methoxy-3α,5-cyclo-5α-24-norcholan-23-ol 23-tosylate 
• 869858-22-0 (25R)-6β-methoxy-24-phenylsulfonyl-3α,5-cyclo-5α-cholestan-26-ol 26-(2'-tetrahydropyranyl) ether 
• 85639-62-9 3α,5-cyclo-22-phenylsulfonyl-5α-23,24-bisnorcholan-6β-ol 6-methyl ether 
• 266309-09-5 3α,5-cyclo-22(R)-phenylsulfonyl-23(R)-hydroxymethyl-5α-26,27-bisnorergost-6β,24-diol 6-methyl ester 
• 266309-07-3 3α,5-cyclo-22(S)-phenylsulfonyl-23(R)-hydroxymethyl-5α-26,27-bisnorergost-6β,24-diol 6-methyl ester 
• 2140-46-7 25-hydroxychlolesterol 
• 63015-89-4 26,27-dinorcholest-5-en-23-yn-3β-ol 
• 58507-66-7 (20S)-(20-Methyl-3β-<(tetrahydropyran-2-yl)oxy>-5-pregnen-21-ol)-p-toluolsulfonat 
• 7494-34-0 27-nor-5-cholesten-3β-ol-25-one 
• 219903-26-1 3α,5-cyclo-5α-cholest-24-en-22-phenylsulfonyl-6β-ol 6-methyl ether 
• 93528-37-1 24(R),25-Epoxycholesterol 
• 77058-74-3 (24S)-24,25-epoxycholesterol 
• 83872-45-1 (20S)-(20-Methyl-5-pregnen-3β,21-diol)-21-p-toluolsulfonat 

Relevant academic research and scientific papers

SYNTHESIS OF CHOLESTEROL AND VITAMIN D3 FROM PHYTOSTEROLS

The present invention discloses novel method for synthesizing vegan cholesterol and vitamin D3 from inexpensive crude phytosterol.

NOVEL METHOD FOR SYNTHESIZING 25-OH CHOLESTEROL/CALCIFEDIOL FROM PHYTOSTEROL

The present invention discloses novel method for synthesizing vegan 25-OH cholesterol/Calcifediol from inexpensive crude phytosterol. According to the method, Phytosterols are reacted to form corresponding i-steroid through tosylation and methanolysis. i-steroid on reductive ozonolysis to C-22 alcohol and conversion via C-22 tosylate to C-22 iodide in good yield. Coupling of C-22 tosylate with Grignard reagent of 4-bromo-2-methyl-2-[(trimethylsilyl)oxy] butane followed by deprotection yielded 25-OH cholesterol. In a process variant, nickel mediated conjugate addition of C-22 iodide to an electron deficient alkene ethyl acrylate and treating corresponding ester with methyl magnesium bromide as means of installing the side chain of 25-OH cholesterol in high yield. Further bromination reaction of 25-OH cholesterol diacetate followed by dehydrobromination using TBAF yielded 25-OH 7-dehydrocholesterol. Further photo reaction of 25-OH 7-dehydrocholesterol in to previtamin D3 using high or medium pressure mercury lamp and subsequent thermal reaction of previtamin D3 to 25-OH vitamin D3(Calcifediol) in good yield.

Synthesis of a Cholesterol Side-Chain Triazole Analogue via 'Click' Chemistry

An efficient preparation of a cholesterol analogue possessing a triazole ring is achieved starting from commercially available stigmasterol. The procedure is based on a [3+2] cycloaddition of a cholesterol possessing a side-chain terminal azide with a ter

Preparation of (25R)- and (25S)-26-functionalized steroids as tools for biosynthetic studies of cholic acids

A new synthesis of both epimeric forms of 26-cholestanoic acids and 26-alcohols containing a 3β-hydroxy-Δ5- or a Δ4-3-keto-functionality in ring A is described starting from stigmasterol or (20S)-3β-acetoxy-pregn-5-en-20-carboxylic a

Further studies on the synthesis of 24(S),25-epoxycholesterol. A new, efficient preparation of desmosterol

Efforts to improve the synthesis of 24(S),25-epoxycholesterol (1) from stigmasterol (3) have included identification of 6α-hydroxy-i-steroid 11 as a byproduct from the ozonolysis of 9 and an attempt to effect conversion of sulfone 14 to diol 18 via Payne rearrangement and nucleophilic trapping of epoxide 25, which led instead to 27 and 28 (97% yield). A more efficient synthesis of 1 was achieved via coupling of cuprate 21 with allylic acetate 31 to give 73% of 16, in the most efficient conversion yet of a C22 intermediate to desmosterol (5) or its acetate 6.

Efficient, stereoselective synthesis of 24(s), 25-epoxycholesterol

Efficient, stereoselective syntheses of 24(S), 25-epoxycholesterol (1) have been developed starting from cholenic acid (4) or stigmasterol (8), both featuring as the key step Sharpless asymmetric dihydroxylation of desmosterol acetate (2). This work permits preparation of gram quantities of 1 for further evaluation as a natural regulator of cholesterol metabolism, specifically, e.g., as a ligand for the LXRα. nuclear receptor.

Synthesis of Steroid 23-Enamino-25-ketones, Potential Intermediates in the Preparation of Vitamins D and Their Analogs

Steroid C23-nitrile oxide has been synthesized for the first time, and its 1,3-dipolar cycloadditions to 2-propynyl alcohol and 2-propynyl bromide have been studied. The obtained adducts can be converted into 23-enamino-25-ketones which may be