190264-64-3

Upstream product

• 46117-43-5 vinyl phenyl carbonate 
• 113375-51-2 (3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene 
• 190264-67-6 (3S,5R)-1-ethynyl-2-methyl-3,5-bis[(vinyloxy)carbonyloxy]-1-cyclohexene 
• 139705-38-7 acetone O-<(vinyloxy)carbonyl>oxime 

Downstream Products

• 190264-76-7 (2-Hydroxy-ethyl)-carbamic acid (1R,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester 
• 190264-75-6 Butyl-carbamic acid (1R,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester 
• 190264-78-9 (3-Amino-propyl)-carbamic acid (1R,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester 
• 190264-74-5 Carbamic acid (1R,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester 
• 916480-03-0 (3S,5R,3'S,5'R)-1,1'-diethynyl-3,3'-dihydroxy-2,2'-dimethyl-5,5'-[butan(1,4-dicarbamoyloxy)]dicyclohex-1-ene 
• 916480-04-1 (3S,5R,3'S,5'R)-1,1'-diethynyl-3,3'-dihydroxy-2,2'-dimethyl-5,5'-[hexan(1,6-dicarbamoyloxy)]dicyclohex-1-ene 
• 916480-05-2 (3S,5R,3'S,5'R)-1,1'-diethynyl-3,3'-dihydroxy-2,2'-dimethyl-5,5'-[dodecane(1,12-dicarbamoyloxy)]dicyclohex-1-ene 
• 916479-99-7 (3S,5R)-5-[N-(4-aminobutyl)carbamoyloxy]-1-ethynyl-3-hydroxy-2-methylcyclohex-1-ene 
• 916480-01-8 (3S,5R)-5-[N-(6-aminohexyl)carbamoyloxy]-1-ethynyl-3-hydroxy-2-methylcyclohex-1-ene 
• 916480-02-9 (3S,5R)-5-[N-(12-aminododecyl)carbamoyloxy]-1-ethynyl-3-hydroxy-2-methylcyclohex-1-ene 
• 916480-08-5 (3S,5R,3'S,5'R)-3,3'-di[(tert-butyldimethylsilyl)oxy]-1,1'-diethynyl-2,2'-dimethyl-5,5'-[dodecane(1,12-dicarbamoyloxy)]dicyclohex-1-ene 
• 916480-07-4 (3S,5R,3'S,5'R)-3,3'-di[(tert-butyldimethylsilyl)oxy]-1,1'-diethynyl-2,2'-dimethyl-5,5'-[hexane(1,6-dicarbamoyloxy)]dicyclohex-1-ene 
• 916480-06-3 (3S,5R,3'S,5'R)-3,3'-di[(tert-butyldimethylsilyl)oxy]-1,1'-diethynyl-2,2'-dimethyl-5,5'-[butane(1,4-dicarbamoyloxy)]dicyclohex-1-ene 

Relevant academic research and scientific papers

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.

Selective Alkoxycarbonylation of A-Ring Precursors of Vitamin D Using Enzymes in Organic Solvents. Chemoenzymatic Synthesis of 1α,25-Dihydroxyvitamin D3 C-5 A-Ring Carbamate Derivatives

A-Ring modification of 1α,25-dihydroxyvitamin D3 [2, 1α,25-(OH)2-D3] is an important area of analog studies to investigate biological activity of vitamin D-related structures. An efficient synthesis of 1α,25-(OH)2-D3 C-5 A-ring carbamate derivatives 19 and amino acid derivatives 21 was developed by applying a two-step chemoenzymatic strategy, involving the enzymatic synthesis of carbonates followed by reaction with amino derivatives. Accordingly, we began the studies of enzymatic alkoxycarbonylation of 1α,25-(OH)2-D3 A-ring precursor 7. Candida antarctica lipase (CAL) was found to be the best catalyst in toluene. Regioselective alkoxycarbonylation occurred only at the C-5-(R) hydroxyl group. Good to excellent yields were achieved by chemical reaction of these carbonates with amino derivatives. The procedure provided convenient synthesis of carbonates 19 and 21 under mild reaction conditions.