405229-45-0

Basic information

• Product Name: (3R,5R)-3,5-diacetoxy-1-ethynyl-2-methylcyclohex-1-ene
• Synonyms: (3R,5R)-3,5-diacetoxy-1-ethynyl-2-methylcyclohex-1-ene
• CAS NO: 405229-45-0
• Molecular Weight: 236.268
• Mol File: 405229-45-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (3R,5R)-3,5-diacetoxy-1-ethynyl-2-methylcyclohex-1-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,5R)-3,5-diacetoxy-1-ethynyl-2-methylcyclohex-1-ene(405229-45-0)
• EPA Substance Registry System: (3R,5R)-3,5-diacetoxy-1-ethynyl-2-methylcyclohex-1-ene(405229-45-0)

Safety Data

• Hazardous Substances Data: 405229-45-0(Hazardous Substances Data)

Upstream product

• 169305-41-3 (5R)-3-Ethynyl-5-hydroxy-2-methyl-2-cyclohexen-1-one 
• 405229-44-9 (3S,5R)-3,5-diacetoxy-1-ethynyl-2-methylcyclohex-1-ene 
• 350985-91-0 (3R,5R)-5-acetoxy-1-ethynyl-2-methyl-3-[(4-nitrophenyl)carbonyloxy]cyclohex-1-ene 
• 113375-51-2 (3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene 
• 108-24-7 acetic anhydride 
• 169437-97-2 (3R,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene 

Downstream Products

• 169437-97-2 (3R,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene 
• 405197-18-4 (3R,5R)-5-acetoxy-1-ethynyl-3-hydroxy-2-methylcyclohex-1-ene 

Relevant articles and documents

Synthesis of monoacyl A-ring precursors of 1α,25-dihydroxyvitamin D3 through selective enzymatic hydrolysis

An efficient synthesis of monoacylated 1α,25-dihydroxyvitamin D3 A-ring precursors 15, 16, 18, and 19 has been described through an enzymatic hydrolysis process. Candida antarctica A lipase (CAL-A) hydrolyzes the C-5 acetate ester in trans stereoisomers 9 and 13, with complete and high selectivity, respectively. In the case of cis isomers 11 and 14, Chromobacterium viscosum lipase (CVL) is the enzyme of choice, exhibiting opposite selectivity for these two enantiomers. This lipase selectively catalyzes the hydrolysis at the C-3 acetate in diester 11 and at C-5 position in diester 14. It is noteworthy that through a hydrolysis reaction CAL-A and CVL allow the synthesis of the four A-ring monoacetylated precursors of 1α,25-dihydroxyvitamin D3, precursors which are complementary to those obtained by the enzymatic acylation process. In addition, with excellent yield CVL selectively hydrolyzes the C-3 chloroacetate ester instead of the C-5 acetate in diester 22, a key intermediate in the synthesis of new A-ring modified 1α,25-dihydroxyvitamin D3 analogues.