108887-35-0

Basic information

• Product Name: 1α,3β-bis(tert-butyldimethylsilyloxy)-9,10-secocholesta-5,7,10(19)-triene
• Synonyms: 1α,3β-bis(tert-butyldimethylsilyloxy)-9,10-secocholesta-5,7,10(19)-triene
• CAS NO: 108887-35-0
• Molecular Weight: 629.17
• Mol File: 108887-35-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1α,3β-bis(tert-butyldimethylsilyloxy)-9,10-secocholesta-5,7,10(19)-triene(CAS DataBase Reference)
• NIST Chemistry Reference: 1α,3β-bis(tert-butyldimethylsilyloxy)-9,10-secocholesta-5,7,10(19)-triene(108887-35-0)
• EPA Substance Registry System: 1α,3β-bis(tert-butyldimethylsilyloxy)-9,10-secocholesta-5,7,10(19)-triene(108887-35-0)

Safety Data

• Hazardous Substances Data: 108887-35-0(Hazardous Substances Data)

Usage

Structure

Steroid skeleton with TBS groups attached at the 1α and 3β positions
The steroid skeleton is based on a cholesterol structure with modifications at the 9,10 double bond.

Tert-Butyldimethylsilyl (TBS) group

A commonly used protecting group in organic synthesis
Provides stability to sensitive functional groups during chemical reactions.

Potential applications

Pharmaceutical industry
The compound has potential applications in the development of new pharmaceutical compounds due to its unique structure and reactivity.

Use

Synthesis of novel steroidal derivatives with potential medicinal properties
The compound serves as an important intermediate in creating new steroidal derivatives with potential therapeutic applications.

Upstream product

• 112670-83-4 (1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-1-((S)-1,5-dimethyl-2-methylselanyl-hexyl)-7a-methyl-octahydro-indene 
• 74055-38-2 Benzoic acid 1-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl]-2-[(1R,3aR,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]-2-(toluene-4-sulfonyl)-ethyl ester 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 74064-29-2 (3R,3aR,7aR)-7-Chloromethyl-3-((R)-1,5-dimethyl-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene 
• 74055-35-9 methyl (3S,5R)-3,5-dihydroxy-2-methylcyclohex-1-ene-1-carboxylate 
• 3752-57-6 8-hydroxymethyl-des-AB-cholest-8-ene p-nitrobenzoate 
• 75211-99-3 8-p-tolylsulphonylmethyl-des-AB-cholest-8-ene 
• 74055-37-1 (1S,5R)-3-hydroxymethyl-4-methylcyclohex-3-ene-1,5-diol bis(t-butyldimethylsilyl) ether 
• 74063-01-7 8-hydroxymethyl-des-AB-cholest-8-ene 
• 74064-30-5 (3S,5R)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-2-methylcyclohex-1-en-1-carboxaldehyde 
• 74055-36-0 methyl (3S,5R)-3,5-bis-t-bytyldimethylsilyloxy-2-methylcyclohex-1-enecarboxylate 
• 31915-47-6 (1S,5S)-2-Methyl-6-oxa-bicyclo[3.2.1]oct-2-en-7-one 
• 55365-49-6 5α,6α-epoxy-6-methylcyclohexane-1β,3β-carbolactone 
• 263712-12-5 (8β)-De-A,B-8-(tert-butyldimethylsilyloxy)-22-cholestyne-24-ol 

Downstream Products

• 41294-56-8 1α-hydroxyvitamin D3 

Relevant articles and documents

Synthesis and pharmacokinetics of 1α-hydroxyvitamin D3 tritiated at 22 and 23 positions showing high specific radioactivity

A novel synthesis of a radioactive compound of 1α-hydroxyvitamin D3 (1αOHD3) (1) and its pharmacokinetics are described. Radioactive 1αOHD3 tritiated at 22 and 23 positions ([22,23-3H4]1αOHD3) (5) was prepared via key reactions of the reduction of acetylenic side chain in the ketone (12) with tritium gas in the presence of palladium-charcoal and the subsequent Wittig reaction with the A-ring synthon (16). [22,23-3H4]1αOHD3 (5) showed high specific radioactivity (111.5 Ci/mmol) and was used successfully in pharmacokinetics studies with rats. In the pharmacokinetics studies, the plasma concentration level of the active form of vitamin D3, 1α,25- dihydroxyvitamin D3 [1α,25(OH)2D3], after oral or intravenous administration of [22,23-3H4]1αOHD3 (5), showed longer half-life, lower maximum concentration, and lower area under the curve than those after treatment of 1α,25(OH)2D3 tritiated at 26 and 27 positions (4). These results might suggest a beneficial therapeutic utility of 1αOHD1 (1) over the treatment of 1α,25(OH)2D3 (2).

Calciferol and its Relatives. Part 27. A Synthesis of 1α-Hydroxyvitamin D3 by way of 1α-Hydroxytachysterol3

A new synthesis of 1α-hydroxyvitamin D3 is described.The bis-t-butyldimethylsilyl ether (17) of (3S,5R)-3,5-dihydroxy-2-methylcyclohex-1-enecarbaldehyde and 8-p-tolylsulphonylmethyl-des-AB-cholest-8-ene (4) were combined to give mixed benzoyloxysulphones which, on reductive elimination with sodium amalgam, gave the corresponding bis-ether of 1α-hydroxytachysterol3.This was isomerised photochemically to the bis-ether of 1α-hydroxyprecalciferol3, and then thermally to give the bis-ether of 1α-hydroxyvitamin D3.Removal of protecting groups gave 1α-hydroxyvitamin D3 (21) in 62percent yield from the sulphone (4), or 12.8percent overall from cholesterol.