250590-23-9

Basic information

• Product Name: (3R,5S)-1-ethynyl-3-hydroxy-2-methyl-5-[(vinyloxy)carbonyloxy]-1-cyclohexene
• Synonyms: (3R,5S)-1-ethynyl-3-hydroxy-2-methyl-5-[(vinyloxy)carbonyloxy]-1-cyclohexene
• CAS NO: 250590-23-9
• Molecular Weight: 222.241
• Mol File: 250590-23-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (3R,5S)-1-ethynyl-3-hydroxy-2-methyl-5-[(vinyloxy)carbonyloxy]-1-cyclohexene(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,5S)-1-ethynyl-3-hydroxy-2-methyl-5-[(vinyloxy)carbonyloxy]-1-cyclohexene(250590-23-9)
• EPA Substance Registry System: (3R,5S)-1-ethynyl-3-hydroxy-2-methyl-5-[(vinyloxy)carbonyloxy]-1-cyclohexene(250590-23-9)

Safety Data

• Hazardous Substances Data: 250590-23-9(Hazardous Substances Data)

Upstream product

• 146728-48-5 (3R,5S)-3,5-dihydroxy-1-ethynyl-2-methylcyclohex-1-ene 
• 797037-96-8 (3R,5S)-1-ethynyl-2-methyl-3,5-bis[(vinyloxy)carbonyloxy]-1-cyclohexene 
• 139705-38-7 acetone O-<(vinyloxy)carbonyl>oxime 

Relevant articles and documents

Regioselective enzymatic syntheses of C-3 and C-5 carbonate A-ring stereoisomeric precursors of vitamin D

The synthesis of selectively modified A-ring precursors for the preparation of 1α,25-dihydroxyvitamin D3 analogues by enzymatic hydrolysis reaction of corresponding dicarbonates has been accomplished. Thus, Candida rugosa lipase (CRL) was found to hydrolyze with high selectivity the C-3 carbonate of stereoisomers 4a,b, and 4d, furnishing C-5 vinyloxycarbonates 5a,b, and 5d. On the other hand, Chromobacterium viscosum lipase exhibit opposite regioselectivity with cis enantiomers 4c and 4d, catalyzing hydrolysis at the C-5 carbonate for 4c and at C-3 position for 4d. In addition, CRL catalyzes the alkoxycarbonylation reaction at C-3 of diol 3d affording the monocarbonate complementary to the one obtained by the enzymatic hydrolysis process.