301153-94-6

Basic information

• Product Name: (3R,5S)-3,5-di[(tert-butyldimethylsilyl)oxy]cyclohex-1-enecarbaldehyde
• Synonyms: (3R,5S)-3,5-di[(tert-butyldimethylsilyl)oxy]cyclohex-1-enecarbaldehyde
• CAS NO: 301153-94-6
• Molecular Weight: 370.68
• Mol File: 301153-94-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3R,5S)-3,5-di[(tert-butyldimethylsilyl)oxy]cyclohex-1-enecarbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,5S)-3,5-di[(tert-butyldimethylsilyl)oxy]cyclohex-1-enecarbaldehyde(301153-94-6)
• EPA Substance Registry System: (3R,5S)-3,5-di[(tert-butyldimethylsilyl)oxy]cyclohex-1-enecarbaldehyde(301153-94-6)

Safety Data

• Hazardous Substances Data: 301153-94-6(Hazardous Substances Data)

Upstream product

• 301153-90-2 methyl (3R,5S)-3,5-di[(p-nitrophenylcarbonyl)oxy]-cyclohex-1-enecarboxylate 
• 301153-92-4 methyl (3R,5S)-3,5-di[(tert-butyldimethylsilyl)oxy]cyclohex-1-enecarboxylate 
• 301153-89-9 methyl (3R,5R)-5-hydroxy-3-[(p-nitrophenylcarbonyl)oxy]-cyclohex-1-enecarboxylate 
• 301153-91-3 methyl (3R,5S)-3,5-dihydroxycyclohex-1-enecarboxylate 
• 262594-24-1 methyl (3R,5R)-5-[(tert-butyldimethylsilyl)oxy]-3-[(p-nitrophenylcarbonyl)oxy]cyclohex-1-enecarboxylate 
• 262594-22-9 methyl (3S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-cyclohex-1-enecarboxylate 
• 262594-23-0 methyl (3S,5R)-5-[(tert-butyldimethylsilyl)oxy]-3-hydroxy-cyclohex-1-enecarboxylate 
• 139356-32-4 methyl (1s_n,3R,4s_n,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-[(imidazol-1-ylthiocarbonyl)oxy]-cyclohexanecarboxylate 
• 139356-33-5 (3S,5S)-3,5-bis[(tert-butyl)dimethylsilyloxy]-1-hydroxycyclohexane-1-carboxylic acid methyl ester 
• 135711-62-5 methyl quinicate 
• 191916-39-9 methyl (-)-quinate 
• 77-95-2 D-(-)-quinic acid 
• 301153-93-5 (3R,5S)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-hydroxymethylcyclohex-1-ene 

Downstream Products

• 301153-99-1 1β,25-dihydroxy-6,7-dehydro-3-epi-19-nor-previtamin D₃ 
• 301153-97-9 (3R,3aR,7aR)-7-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylethynyl]-3-((R)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene 
• 301153-95-7 (3R,5S)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-ethynylcyclohex-1-ene 

Relevant articles and documents

6-s-cis locked analogues of the steroid hormone 1α,25-dihydroxyvitamin D3. Synthesis of novel A-ring stereoisomeric 1,25-dihydroxy-3-epi-19-nor-previtamin D3 derivatives

Efficient syntheses of A-ring synthons 24 and 32 are described from hydroxy ester 16, which is easily available on a preparative scale from (-)-quinic acid. Key features of the syntheses were (a) the ability to selectively perform desilylations in the presence of p-nitrobenzoate esters and (b) the excellent yield and complete stereospecificity with which the configuration of alcohols 16, 18, and 26 could be inverted under Mitsunobu conditions. Thus, A-ring synthons 24 and 32 were both prepared in 35-38% yield (eight steps) from the common precursor 16. The coupling of A-ring synthons 24 and 32 with the appropriate CD-ring/side chain fragment 7 provides access to novel 6-s-cis locked analogues of steroid hormone 1α,25-dihydroxyvitamin D3: 1α,25-dihydroxy-3-epi-19-nor-previtamin D3 (37) and 1β,25-dihydroxy-3-epi-19-nor-previtamin D3 (38), which are unable to undergo rearrangement to the respective vitamin D form by virtue of the absence of the C-19 methyl group. Compounds 37 and 38 can be used as tools for studying the genomic and nongenomic mechanisms of action of the previtamin form of the hormone 1α,25-dihydroxyvitamin D3.