129482-80-0

Basic information

• Product Name: methyl (Z,3S,5R)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]acetate
• Synonyms: methyl (Z,3S,5R)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]acetate
• CAS NO: 129482-80-0
• Molecular Weight: 426.744
• Mol File: 129482-80-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl (Z,3S,5R)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]acetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (Z,3S,5R)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]acetate(129482-80-0)
• EPA Substance Registry System: methyl (Z,3S,5R)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]acetate(129482-80-0)

Safety Data

• Hazardous Substances Data: 129482-80-0(Hazardous Substances Data)

Upstream product

• 129482-79-7 [(2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(2-nitro-phenylselanylmethyl)-cyclohex-(Z)-ylidene]-acetic acid methyl ester 
• 121961-83-9 Sodium; (1S,6R)-6-hydroxymethyl-cyclohex-3-enecarboxylate 
• 129482-76-4 (4R,4aS,6R,8S,8aR)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-4-phenylselanyl-octahydro-isochromen-3-one 
• 129482-78-6 [(2R,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-(Z)-ylidene]-acetic acid methyl ester 
• 129482-77-5 (6R,8S,8aR)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-1,5,6,7,8,8a-hexahydro-isochromen-3-one 
• 129482-74-2 C₂₄H₄₈O₃S₂Si₂ 
• 546125-82-0 (4aR,6R,8S,8aR)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-octahydro-isochromen-3-one 
• 129482-71-9 (1S,2R,4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-[1,3]dithian-2-ylidenemethyl-7-oxa-bicyclo[4.1.0]heptan-2-ol 
• 130595-59-4 (1S,2R,4R,5R)-2-<(tert-Butyldimethylsilyloxy)methyl>-4-iodo-6-oxabicyclo<3.2.1>octan-7-one 
• 129482-69-5 (1R,2R,5R)-2-<(tert-Butyldimethylsilyloxy)methyl>-6-oxabicyclo<3.2.1>oct-3-en-7-one 
• 129482-72-0 (1R,3S,4R,5S)-5-[1,3]Dithian-2-ylidenemethyl-4-hydroxymethyl-cyclohexane-1,3-diol 
• 31139-02-3 (1R,6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid 
• 129482-73-1 C₁₂H₂₀O₃S₂ 
• 130695-72-6 (1S,2R,4R,5R)-2-Hydroxymethyl-4-iodo-6-oxabicyclo<3.2.1>octan-7-one 

Downstream Products

• 81506-24-3 [3S-(1Z,3α,5β)]-2-[3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethanol 

Relevant articles and documents

Synthesis and evaluation of A-ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D3 (OCT)

A-ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D3 (OCT) (2), 3-epi-1α,25-dihydroxy-22-oxavitamin D3 (3-epiOCT) (3) and 1,3-diepi-1α,25-dihydroxy-22-oxavitamin D3 (1,3-diepiOCT) (4) were synthesized by the convergent method. In vitro binding affinity for rat vitamin D binding protein and calf-thymus vitamin D receptor, differentiation-inducing activity on HL-60 cells, and transcriptional activity of 3-epiOCT (3) and 1,3-diepiOCT (4) were evaluated in comparison with OCT (2), 1-epi-1α,25-dihydroxy-22-oxavitamin D3 (1-epiOCT) (5) and 1α,25-dihydroxyvitamin D3 (1).

An Efficient Asymmetric Synthesis of 1α,25-(OH)2 Vitamin D3 A-Ring Synthon

Chiral synthesis of the A-ring synthon 3 of 1α,25-dihydroxyvitamin D3 (1a) based on palladium-catalyzed cyclization of 8-bromo-2,8-nonadienoates is described.Reaction of (E)-4b and (Z)-4d in the presence of Pd(OAc)2, PPh3 and K2CO3 gave (E)-3b and (Z)-3d, respectively.Optically active 4d was prepared from 24 by asymmetric aldol reaction using 31, which was cyclized to 3d.With further reactions, 1α,25-dihydroxyvitamin D3 (1a) was obtained.

An enantioselective synthesis of the A-ring synthon for vitamin D3 metabolites by chemicoenzymatic approach

The A-ring synthon for vitamin D3 metabolites having 1α-hydroxyl group is synthesized starting from a chiral monoester 6 enzymatically generated.