(3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester

Base Information

Chemical Name:(3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester
CAS No.:186767-30-6
Molecular Formula:C₁₄H₂₆O₅Si
Molecular Weight:302.443
Hs Code.:

Synonyms:(3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester

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Chemical Property of (3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester

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Technology Process of (3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester

There total 6 articles about (3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enecarboxylic 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: 76.0%

: 186767-26-0
(S)-5-(tert-Butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienecarboxylic acid methyl ester

: 186767-30-6
(3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; In tetrahydrofuran; water; at 0 ℃;
DOI:10.1016/S0040-4039(96)02259-9

Reference yield:

: 245680-45-9
(1S,2S,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carbothioic acid S-ethyl ester

: 186767-30-6
(3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 93 percent / Cs₂CO₃ / 0 °C

2.1: LiHMDS / tetrahydrofuran / -78 - 0 °C

2.2: 90 percent / 2,6-lutidine / tetrahydrofuran / -78 °C

3.1: 74 percent / aq. OsO₄; NMO / tetrahydrofuran / 0 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; caesium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; 1.1: transesterification / 2.1: Ring cleavage / 2.2: silylation / 3.1: dihydroxylation;
DOI:10.1021/ja991191c

Reference yield:

: 186666-50-2
3-((1S,2S,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one

: 186767-30-6
(3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrahydrofuran / -20 °C

2.1: 93 percent / Cs₂CO₃ / 0 °C

3.1: LiHMDS / tetrahydrofuran / -78 - 0 °C

3.2: 90 percent / 2,6-lutidine / tetrahydrofuran / -78 °C

4.1: 74 percent / aq. OsO₄; NMO / tetrahydrofuran / 0 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; caesium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; 1.1: transesterification / 2.1: transesterification / 3.1: Ring cleavage / 3.2: silylation / 4.1: dihydroxylation;
DOI:10.1021/ja991191c