(1R,3S,4R,5R)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-2-oxo-cyclohexanecarboxylic acid methyl ester

Base Information

Chemical Name:(1R,3S,4R,5R)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-2-oxo-cyclohexanecarboxylic acid methyl ester
CAS No.:215929-10-5
Molecular Formula:C₁₆H₂₈O₈Si
Molecular Weight:376.479
Hs Code.:

Synonyms:(1R,3S,4R,5R)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-2-oxo-cyclohexanecarboxylic acid methyl ester

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Chemical Property of (1R,3S,4R,5R)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-2-oxo-cyclohexanecarboxylic acid methyl ester

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Technology Process of (1R,3S,4R,5R)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-2-oxo-cyclohexanecarboxylic acid methyl ester

There total 5 articles about (1R,3S,4R,5R)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-2-oxo-cyclohexanecarboxylic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

: 215929-09-2
(1R,5R)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-3-enecarboxylic acid methyl ester

: (1R,3R,4S,5R)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-2-oxo-cyclohexanecarboxylic acid methyl ester

: 215929-10-5
(1R,3S,4R,5R)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-2-oxo-cyclohexanecarboxylic acid methyl ester

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; water; In tetrahydrofuran; at 0 ℃; for 72h;
DOI:10.1039/a805775c

Reference yield:

: 171824-23-0
(-)-(1S,4R,4aS,5R,8aR)-5-tert-Butyldimethylsilyloxy-1,4,4a,6,7,8a-hexahydro-endo-1,4-methanonaphthalen-8(5H)-one

: 215929-10-5
(1R,3S,4R,5R)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-2-oxo-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / NaH / tetrahydrofuran / 23 h / Ambient temperature

2: 90 percent / O₂, KF, P(OEt)3 / dimethylsulfoxide / 22 h / Ambient temperature

3: 100 percent / pyridine / 38 h / Ambient temperature

4: 100 percent / diphenyl ether / 1 h / 280 °C

5: 86 percent / OsO₄, NMO, H₂O / tetrahydrofuran / 72 h / 0 °C

With pyridine; potassium fluoride; osmium(VIII) oxide; N-methyl-2-indolinone; water; oxygen; sodium hydride; triethyl phosphite; In tetrahydrofuran; diphenylether; dimethyl sulfoxide;
DOI:10.1039/a805775c

Reference yield:

: 215929-06-9
(1R,4S,4aR,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-1,4,4a,7,8,8a-hexahydro-1,4-methano-naphthalene-6-carboxylic acid methyl ester

: 215929-10-5
(1R,3S,4R,5R)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-2-oxo-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / O₂, KF, P(OEt)3 / dimethylsulfoxide / 22 h / Ambient temperature

2: 100 percent / pyridine / 38 h / Ambient temperature

3: 100 percent / diphenyl ether / 1 h / 280 °C

4: 86 percent / OsO₄, NMO, H₂O / tetrahydrofuran / 72 h / 0 °C

With pyridine; potassium fluoride; osmium(VIII) oxide; N-methyl-2-indolinone; water; oxygen; triethyl phosphite; In tetrahydrofuran; diphenylether; dimethyl sulfoxide;
DOI:10.1039/a805775c