121289-19-8

Basic information

• Product Name: 6-tert-ButyldiMethylsilyloxy-4-(1-Methylethenyl)-1-Methyl-cyclohexane 1,2-Epoxide
• Synonyms: 6-tert-ButyldiMethylsilyloxy-4-(1-Methylethenyl)-1-Methyl-cyclohexane 1,2-Epoxide;(1,1-DiMethylethyl)diMethyl[[(1R,2S,4R,6R)-1-Methyl-4-(1-Methylethenyl)-7-oxabicyclo[4.1.0]hept-2-yl]oxy]-silane
• CAS NO: 121289-19-8
• Molecular Formula: C₁₆H₃₀O₂Si
• Molecular Weight: 282.4937
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 121289-19-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: 6-tert-ButyldiMethylsilyloxy-4-(1-Methylethenyl)-1-Methyl-cyclohexane 1,2-Epoxide(CAS DataBase Reference)
• NIST Chemistry Reference: 6-tert-ButyldiMethylsilyloxy-4-(1-Methylethenyl)-1-Methyl-cyclohexane 1,2-Epoxide(121289-19-8)
• EPA Substance Registry System: 6-tert-ButyldiMethylsilyloxy-4-(1-Methylethenyl)-1-Methyl-cyclohexane 1,2-Epoxide(121289-19-8)

Safety Data

• Hazardous Substances Data: 121289-19-8(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Liquid

Uses

Intermediate in the preparation of Dihydroxyvitamin D3 and associated metabolites.

Upstream product

• 35692-59-2 (1S,2S,4S,6R)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-ol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 6485-40-1 (R)-Carvone 
• 36616-60-1 (1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one 

Downstream Products

• 121289-20-1 (1S,2S,4R,6R)-2,4-bis(tert-butyldimethylsilyloxy)-1-methyl-7-oxabicyclo[4.1.0]heptane 
• 121314-05-4 1-{(Z)-2-[(1R,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-vinyloxymethyl}-4-methoxy-benzene 
• 121289-24-5 (S)-1-[(1S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-2-(4-methoxy-benzyloxy)-ethanol 
• 121289-27-8 1-{2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethoxymethyl}-4-methoxy-benzene 
• 132870-52-1 Methanesulfonic acid (1R,3S,5S)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl ester 
• 121289-28-9 (S)-1-[(1S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-ethane-1,2-diol 
• 81506-24-3 [3S-(1Z,3α,5β)]-2-[3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethanol 
• 121289-22-3 (4R,6S)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-1-iodomethyl-cyclohexene 
• 74064-30-5 (3S,5R)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-2-methylcyclohex-1-en-1-carboxaldehyde 
• 205681-14-7 (2R,5R,7R,9S,10S)-7-guanin-9-yl-5-benzyloxy-2-phenylhexahydrobenzo[1.3]dioxine 
• 205681-11-4 (2R,5R,7R,9S,10S)-7-adenin-9-yl-5-benzyloxy-2-phenylhexahydrobenzo[1.3]dioxine 
• 205681-15-8 (1S,2R,3R,5S)-5-guanin-9-yl-3-benzyloxy-2-(hydroxymethyl)cyclohexanol 
• 205681-12-5 (1S,2R,3R,5S)-5-adenin-9-yl-3-benzyloxy-2-(hydroxymethyl)cyclohexanol 
• 205681-07-8 (2R,5R,7R,9S,10S)-5-benzyloxy-7-(tert-butyldimethylsilyloxy)-2-phenylhexahydrobenzo[1.3]dioxine 

Relevant articles and documents

Stereoselective synthesis of enantiomerically pure, orthogonally protected 2-methylenecyclohexane-1,3,5-triols and 2,4,6-trihydroxycyclohexanones

The triply silyl protected 2-methylenecyclohexane-1,3,5-triols 1a-c (C-1: tert-butyldimethylsilyl, TBDMS; C-3: trimethylsilyl, TMS; C-5: tert-butyldiphenylsilyl, TBDPS) were prepared from (R)-(-)-carvone in seven synthetic steps (overall yields: 29-53%). Ozonolysis in the presence of triethylamine yielded the triply protected 2,4,6-trihydroxycyclohexanones 2a-c (85%-quant.). The configuration of the products was proven by NOESY studies and by chemical correlation.

Enantioselective approach to the synthesis of cyclohexane carbocyclic nucleosides

(R)-(-)-Carvone was used as starting material for the synthesis of a new series of 2-(hydroxymethyl)-cyclohexane-1,3-diol nucleosides. The enantioselective precursors of the nucleoside analogues were obtained via a stereo- and regioselective hydroboration reaction. The compounds have equatorial oriented base moieties despite the presence of three other axial substituents.