51231-23-3

Basic information

• Product Name: (3β,5α,6β,20S)-6-Methoxy-3,5-cyclopregnane-20-Methanol
• Synonyms: (3β,5α,6β,20S)-6-Methoxy-3,5-cyclopregnane-20-Methanol;FHAMDNXTPYSJGZ-WGRYGTHWSA-N
• CAS NO: 51231-23-3
• Molecular Formula: C₂₃H₃₈O₂
• Molecular Weight: 346.54662
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 51231-23-3.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3β,5α,6β,20S)-6-Methoxy-3,5-cyclopregnane-20-Methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (3β,5α,6β,20S)-6-Methoxy-3,5-cyclopregnane-20-Methanol(51231-23-3)
• EPA Substance Registry System: (3β,5α,6β,20S)-6-Methoxy-3,5-cyclopregnane-20-Methanol(51231-23-3)

Safety Data

• Hazardous Substances Data: 51231-23-3(Hazardous Substances Data)

Usage

Description

(3β,5α,6β,20S)-6-Methoxy-3,5-cyclopregnane-20-Methanol is a functionalized steroid compound derived from the cyclopregnane family of steroids. It is characterized by its unique molecular structure, featuring a 3β-hydroxyl group, a 5α-hydroxyl group, a 6β-methoxy group, and a 20S-configuration. (3β,5α,6β,20S)-6-Methoxy-3,5-cyclopregnane-20-Methanol is known for its potential applications in various fields, particularly in the biosynthetic studies of cholic acids and vitamin D3 derivatives.

Uses

Used in Pharmaceutical Industry:
(3β,5α,6β,20S)-6-Methoxy-3,5-cyclopregnane-20-Methanol is used as a precursor in the synthesis of cholic acids and vitamin D3 derivatives for the pharmaceutical industry. Its unique structural features make it a valuable tool in the development of new drugs and therapeutic agents.
Used in Research and Development:
In the field of research and development, (3β,5α,6β,20S)-6-Methoxy-3,5-cyclopregnane-20-Methanol serves as a key intermediate in the biosynthetic studies of various steroidal compounds. Its role in understanding the synthesis and biological activities of cholic acids and vitamin D3 derivatives contributes to the advancement of knowledge in steroid chemistry and related fields.
Used in Chemical Synthesis:
(3β,5α,6β,20S)-6-Methoxy-3,5-cyclopregnane-20-Methanol is also utilized as a building block in the chemical synthesis of other complex steroidal molecules. Its versatile structure allows for further functionalization and modification, enabling the creation of novel compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 53603-94-4 stigmasterol methyl ether 
• 119005-06-0 (E)-21-(((bromomethyl)dimethylsilyl)oxy)-6β-methoxy-3α,5α-cyclopregn-17(20)-ene 
• 119005-07-1 (Z)-21-(((bromomethyl)dimethylsilyl)oxy)-6β-methoxy-3α,5α-cyclopregn-17(20)-ene 
• 84927-51-5 (17E)-6β-methoxy-3α,5-cyclo-5α-pregn-17(20)-en-16β-ol 
• 101387-33-1 (20R)-20-hydroxymethyl-6β-methoxy-3α,5-cyclo-5α-pregn-16-ene 
• 139894-63-6 22,23-dihydrostigmasteryl methyl ether 
• 83-48-7 Stigmasterol 
• 53139-42-7 stigmasteryl tosylate 
• 53-43-0 dehydroepiandrosterone 
• 73668-91-4 (17E)-6β-methoxy-3α,5-cyclo-5α-pregn-17(20)-en-16α-ol 
• 139871-19-5 (3β,17Z)-3-{[(tert-butyl)dimethylsilyl]oxy}-pregna-5,17(20)-diene 
• 69454-82-6 3β-tert-butyldimethylsilyloxy-20(R)-hydroxy-pregna-5-ene 
• 69454-81-5 3β-tert-butyldimethylsilyloxy-20(S)-hydroxy-pregna-5-ene 
• 979-02-2 16-dehydropregnenolone acetate 

Downstream Products

• 25819-77-6 (20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde 
• 51231-24-4 (20S)-(6β-Methoxy-20-methyl-3α,5-cyclo-5α-pregnan-21-ol)-p-toluolsulfonat 
• 869858-22-0 (25R)-6β-methoxy-24-phenylsulfonyl-3α,5-cyclo-5α-cholestan-26-ol 26-(2'-tetrahydropyranyl) ether 
• 824397-22-0 (24S)-[26,27-2H6]6β-methoxy-23-phenylsulfonyl-24-methyl-3α,5-cyclo-5α-cholestan-22-ol 
• 824397-28-6 (24S)-[26,27-2H6]6β-methoxy-23-phenylsulfonyl-24-methyl-3α,5-cyclo-5α-cholestan-22-one 
• 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 
• 77058-74-3 (24S)-24,25-epoxycholesterol 
• 93528-37-1 24(R),25-Epoxycholesterol 
• 219903-26-1 3α,5-cyclo-5α-cholest-24-en-22-phenylsulfonyl-6β-ol 6-methyl ether 
• 27460-26-0 24(R)-Hydroxycholesterol 
• 90211-85-1 (24R)-6β-methoxy-22-phenylsulfonyl-24-hydroxy-3α,5α-cyclocholestane 
• 90211-86-2 (24S)-6β-methoxy-22-phenylsulfonyl-24-benzyloxy-3α,5α-cyclocholestane 

Relevant articles and documents

A convenient synthesis of the side-chain of sterols

Potassium t-butoxide-induced Ramberg-Backlund rearrangement of chlorosulfones formed from a cyclopregnane-20-thiomethanol derivative has been shown to give Δ22-unsaturated steroids with high trans stereoselectivity.

On the mechanism of the dyotropic expansion of hydrindanes into decalins

A combined computational/experimental approach has revealed key mechanistic aspects in a recently reported dyotropic expansion of hydrindanes into decalins. While computer simulations had already anticipated the need for acid catalysis for making this reaction feasible under the mild conditions used in the laboratory, this work places the dyotropic step not into the reaction flask but at a later step, during the work up instead. With this information in hand the reaction has been optimized by exploring the performance of different activating agents and shown to be versatile, particularly in steroid related chemistry due to the two scaffolds that this reaction connects. Finally, the scope of the reaction has been significantly broadened by showing that this protocol can also operate in the absence of the fused six-member ring.

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