35692-59-2

Usage

Chemical Properties

Pale Yellow Oil

Upstream product

• 36616-60-1 (1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one 
• 6485-40-1 (R)-Carvone 

Downstream Products

• 191410-13-6 1-((1R,3S,5R,6S)-5-Hydroxy-6-methyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-ethanone 
• 122940-84-5 1-((1R,3S,5S,6R)-5-Benzyloxy-6-methyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-ethanone 
• 122940-85-6 Acetic acid 1-((1R,3S,5R)-3-benzyloxy-5-hydroxy-4-methylene-cyclohexyl)-ethyl ester 
• 122940-89-0 Acetic acid 1-((1R,3S,5S,6R)-5-benzyloxy-6-methyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-ethyl ester 
• 122966-26-1 1-((1S,3S,5R)-3-Benzyloxy-5-methoxymethoxy-4-methylene-cyclohexyl)-ethanone 
• 122966-27-2 1-((1S,3S,5R)-3-Benzyloxy-5-methoxymethoxy-4-methylene-cyclohexyl)-2-hydroxy-ethanone 
• 122940-88-9 4-((1S,3S,5R)-3-Benzyloxy-5-methoxymethoxy-4-methylene-cyclohexyl)-[1,3]dioxolan-2-one 
• 1154606-95-7 tert-butyl{[(1R,2R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]hept-2-yl]oxy}diphenylsilane 
• 57429-67-1 3,5-dinitrobenzoate ester of (+)-trans-carveol 
• 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 

Relevant academic research and scientific papers

Titanocene-promoted stereoselective eliminations on epoxy alcohols derived from R-(-)-carvone

The reaction of several stereoisomeric epoxy alcohols, obtained from R-(-)-carvone, and their corresponding formates, acetates, and benzoates, promoted by Cp2TiCl has been studied. The different outcomes of the reaction of epoxy derivatives are rationalized in terms of mechanistically biased processes. The radicals emerging from oxirane cleavage provide two types of reaction: dehydroxylation (deoxycarbonylation) and dehydrogenation. The results offer considerable support for the radical elimination theory of hydroxyl, formyloxyl, and acetoxyl groups. The inability of tertiary radicals to be reduced by the Ti(III) complex is demonstrated unequivocally.

VITAMIN D RECEPTOR ACTIVATORS AND METHODS OF MAKING

The invention relates to compounds that are vitamin D receptor activators, compositions comprising such compounds, methods of using such compounds and compositions, processes for preparing such compounds, and intermediates obtained during such processes.

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.

A novel and enantioselective approach to the synthesis of cyclohexane carbocyclic nucleosides starting from (-)-carvone

3,5-dihydroxy-4-(hydroxymethyl)-1-cyclohexanyl adenine has been synthesized starting from (-)-carvone. The adenine base was introduced via Mitsunobu reaction. Conformational analysis showed that the base still adopts the equatorial position at the expense of three axial substituents.

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.

Efficient and versatile synthesis of A-ring precursors of 1α,25-dihydroxyvitamin D3 and analogues. Application to the synthesis of Lythgoe-Roche phosphine oxide

An efficient, versatile synthesis of Lythgoe-Phosphine Oxide has been developed starting from l-carvene. The key steps are rupture of protected epoxide 7 to give dicarbonyl compound 8, preparation of vinylic triflate 2, and palladium-catalysed cyclization-carbonylation of vinylic triflate 2.

(R)-Carvone as chiral template for the synthesis of some polyols

Some (4S,6R,7R) 4,6,7-trihydroxyheptyl derived building blocks have been obtained from (R)-carvone as the chiral template.A key-step is the Baeyer-Villiger oxidation of a suitable intermediate.

Synthesis of the four epimeric tosylates of (5R)-2,3-epoxy-5-isopropenyl-cyclohexanol

Described is the synthesis of the four optically pure epoxytosylates 5, 6, 9 and 12, each with four chiral centers determined, from a single starting material, (R)(-) carvone.

Efficient Enantiospecific Synthesis of Key A-Ring Synthons for the Preparation of 1α,25-Dihydroxyvitamin D3 Using a Chromium((II)-Mediated Reaction

Key A-ring synthons for the synthesis of 1α,25-dihydroxyvitamin D3 have been prepared efficiently from (R)-(-)-carvone by use of diastereoselective chromium(II)-mediated addition of an allylic halide to an aldehyde as a key step.