(2S,3R,4R,5R)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-methyl-hexanoic acid methyl ester

Base Information

Chemical Name:(2S,3R,4R,5R)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-methyl-hexanoic acid methyl ester
CAS No.:212767-77-6
Molecular Formula:C₂₁H₃₆O₆Si
Molecular Weight:412.599
Hs Code.:

Synonyms:(2S,3R,4R,5R)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-methyl-hexanoic acid methyl ester

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Chemical Property of (2S,3R,4R,5R)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-methyl-hexanoic acid methyl ester

Chemical Property:

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Technology Process of (2S,3R,4R,5R)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-methyl-hexanoic acid methyl ester

There total 3 articles about (2S,3R,4R,5R)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-methyl-hexanoic 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:

: 216868-37-0
(2R,3R)-4-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylbutan-1-ol

: 212767-77-6
(2S,3R,4R,5R)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-methyl-hexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 °C

2: 86 percent / CH₂Cl₂ / 14 h / Heating

3: (DHQD)2PHAL, K₃Fe(CN)6, K₂CO₃, OsO₄, MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 4 h

With osmium(VIII) oxide; methanesulfonamide; potassium carbonate; Dess-Martin periodane; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In dichloromethane; water; tert-butyl alcohol;
DOI:10.1016/S0040-4020(98)00800-X

Reference yield:

: 216868-38-1
(2S,3R)-4-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-2-methylbutanal

: 212767-77-6
(2S,3R,4R,5R)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-methyl-hexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / CH₂Cl₂ / 14 h / Heating

2: (DHQD)2PHAL, K₃Fe(CN)6, K₂CO₃, OsO₄, MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 4 h

With osmium(VIII) oxide; methanesulfonamide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In dichloromethane; water; tert-butyl alcohol;
DOI:10.1016/S0040-4020(98)00800-X

Reference yield:

: (R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyric acid isopropyl ester

: 212767-77-6
(2S,3R,4R,5R)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-methyl-hexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 60 percent / DIBALH / cyclohexane; tetrahydrofuran / 4.5 h / -78 °C

2: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 °C

3: 86 percent / CH₂Cl₂ / 14 h / Heating

4: (DHQD)2PHAL, K₃Fe(CN)6, K₂CO₃, OsO₄, MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 4 h

With osmium(VIII) oxide; methanesulfonamide; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In tetrahydrofuran; dichloromethane; cyclohexane; water; tert-butyl alcohol;
DOI:10.1016/S0040-4020(98)00800-X