113375-51-2

Basic information

• Product Name: (3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene
• Synonyms: (3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene
• CAS NO: 113375-51-2
• Molecular Weight: 152.193
• Mol File: 113375-51-2.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene(113375-51-2)
• EPA Substance Registry System: (3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene(113375-51-2)

Safety Data

• Hazardous Substances Data: 113375-51-2(Hazardous Substances Data)

Upstream product

• 190264-67-6 (3S,5R)-1-ethynyl-2-methyl-3,5-bis[(vinyloxy)carbonyloxy]-1-cyclohexene 
• 39903-97-4 (S)-carvone oxide 
• 18383-51-2 (-)-trans-carveol 
• 6485-40-1 (R)-Carvone 
• 115540-13-1 Acetic acid (1S,2R,4S,6S)-2-ethynyl-4-[1-methoxy-1-(4-nitro-benzoylperoxy)-ethyl]-1-methyl-7-oxa-bicyclo[4.1.0]hept-2-yl ester 
• 115540-12-0 Acetic acid (1S,2R,4S,6S)-2-ethynyl-4-(1-hydroperoxy-1-methoxy-ethyl)-1-methyl-7-oxa-bicyclo[4.1.0]hept-2-yl ester 
• 115540-11-9 (1S,2R,4S,6S)-2-acetoxy-2-ethynyl-4-isopropenyl-1-methyl-7-oxabicyclo<4.1.0>heptane 
• 115540-10-8 (1S,2R,4S,6S)-2-ethynyl-2-hydroxy-4-isopropenyl-1-methyl-7-oxabicyclo<4.1.0>heptane 
• 113375-50-1 (3S,5R)-5-Acetoxy-3-hydroxy-2-methylcyclohex-1-ene-1-carboxaldehyde 
• 113375-49-8 (1R,2S,4R,6S)-2-Hydroxymethyl-4-acetoxy-1-methyl-7-oxabicyclo<4.1.0>heptane 
• 55448-87-8 (3S,5R)-3,5-Diacetoxy-2-methylcyclohex-1-ene-1-carboxaldehyde 
• 113375-48-7 (1R,2S,4R,6S)-2-Hydroxymethyl-4-acetyl-1-methyl-7-oxabicyclo<4.1.0>heptane 
• 113375-47-6 (1R,2S,4R,6S)-2-Hydroxymethyl-1-methyl-4-(1-methylethenyl)-7-oxybicyclo<4.1.0>heptane 
• 4895-08-3 (1R,5R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-methanol 

Downstream Products

• 134328-85-1 6,7-Dehydro-1α-hydroxyprevitamin D₃ 
• 115540-15-3 (1S,5R)-5-acetoxy-1-ethynyl-3-hydroxy-2-methylcyclohex-1-ene 
• 169305-41-3 (5R)-3-Ethynyl-5-hydroxy-2-methyl-2-cyclohexen-1-one 
• 190264-67-6 (3S,5R)-1-ethynyl-2-methyl-3,5-bis[(vinyloxy)carbonyloxy]-1-cyclohexene 
• 122172-39-8 (1S,3S)-bis<(tert-butyldimethylsilyl)oxy>-9,10-secocholesta-5(10),9(11),25-trien-6-yn-8β-yl benzoate 
• 122172-38-7 (1S,3S)-bis<(tert-butyldimethylsilyl)oxy>-9,10-secocholesta-5(10),9(11),25-trien-6-yn-8β-ol 
• 122172-46-7 (3S,5R)-3-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-5-hydroxy-2-methylcyclohex-1-ene 
• 122172-47-8 (3S,5R)-5-<(tert-butyldimethylsilyl)oxy>-1-ethynyl-3-hydroxy-2-methylcyclohex-1-ene 
• 134458-48-3 1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxy-9,14,19,19,19-pentadeuterioprevitamin D3 (tert-butyldiphenyl)silyl ether 
• 134458-47-2 1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxyprevitamin D3 (tert-butyldiphenyl)silyl ether 
• 134458-43-8 (3S,5R)-3,5-bis<((tert-butyldiphenyl)silyl)oxy>-1-(2,2-dibromoethenyl)-2-(trideuteriomethyl)cyclohex-1-ene 
• 134458-41-6 (3S,5R)-3,5-bis<((tert-butyldiphenyl)silyl)oxy>-1-formyl-2-(trideuteriomethyl)cyclohex-1-ene 
• 134485-16-8 (3'S,5'R)-N-<1-<3',5'-bis<((tert-butyldiphenyl)silyl)oxy>-2'-methylcyclohexen-1'-yl>methylidene>butylamine 
• 134458-39-2 (3S,5R)-3,5-bis<((tert-butyldiphenyl)silyl)oxy>-1-ethynyl-2-(trideuteriomethyl)cyclohex-1-ene 

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.

Selective acylation of A-ring precursors of vitamin D using enzymes in organic solvents

Whereas Chromobacterium viscosum lipase (CVL) catalyzes selectively the acylation of the C-5 hydroxyl of the three stereoisomeric vitamin D A-ring precursors 2a, 3a and 3b, only the C-3 hydroxyl of the fourth stereoisomer 2b is acylated under the same conditions in organic solvent. In a convenient application, the racemic vitamin D A-ring precursor 4, possessing only the C-5 hydroxyl, was resolved using suitable conditions identified from the studies of 2 and 3.

Palladium-catalysed coupling of vinyl triflates with enynes and its application to the synthesis of 1α,25-dihydroxyvitamin D3

We describe a general approach, based on the palladium-catalysed coupling of enynes with vinyl triflates, for the construction of dienynes related to vitamin D metabolites and analogues. As an application of this method, an efficient convergent synthesis of 1α,25-dihydroxyvitamin D3 starting from the Inhoffen-Lythgoe diol (6a) and natural carvones has been carried out (11 steps, 28% overall yield from 6a). This strategy allows labelling of the side chain in the final steps of the synthesis.