(S)-tert-butyl 4-((1S,2R,3S)-1-(benzyloxy)-2,3-dihydroxy-4-(tosyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate

Base Information

Chemical Name:(S)-tert-butyl 4-((1S,2R,3S)-1-(benzyloxy)-2,3-dihydroxy-4-(tosyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate
CAS No.:1274699-61-4
Molecular Formula:C₂₈H₃₉NO₉S
Molecular Weight:565.685
Hs Code.:

Synonyms:(S)-tert-butyl 4-((1S,2R,3S)-1-(benzyloxy)-2,3-dihydroxy-4-(tosyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate

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Chemical Property of (S)-tert-butyl 4-((1S,2R,3S)-1-(benzyloxy)-2,3-dihydroxy-4-(tosyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate

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Technology Process of (S)-tert-butyl 4-((1S,2R,3S)-1-(benzyloxy)-2,3-dihydroxy-4-(tosyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate

There total 5 articles about (S)-tert-butyl 4-((1S,2R,3S)-1-(benzyloxy)-2,3-dihydroxy-4-(tosyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate 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%

: 1274699-59-0
(S)-tert-butyl 4-((1S,2R,3S)-1-(benzyloxy)-2,3,4-trihydroxybutyl)-2,2-dimethyloxazolidine-3-carboxylate

: 98-59-9
p-toluenesulfonyl chloride

: 1274699-61-4
(S)-tert-butyl 4-((1S,2R,3S)-1-(benzyloxy)-2,3-dihydroxy-4-(tosyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:: With 1-methyl-1H-imidazole; In dichloromethane; at 0 ℃; for 4h; Inert atmosphere;
DOI:10.1039/c0ob00747a

Reference yield:

: 1274699-53-4
(S)-tert-butyl 4-((R)-1-(benzyloxy)-4-hydroxybut-2-yn-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

: 1274699-61-4
(S)-tert-butyl 4-((1S,2R,3S)-1-(benzyloxy)-2,3-dihydroxy-4-(tosyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene / 0 °C / Inert atmosphere

2.1: osmium(VIII) oxide; citric acid / water; acetone / 20 °C

2.2: 6 h / 20 °C

3.1: 1-methyl-1H-imidazole / dichloromethane / 4 h / 0 °C / Inert atmosphere

With 1-methyl-1H-imidazole; osmium(VIII) oxide; sodium bis(2-methoxyethoxy)aluminum hydride; citric acid; In tetrahydrofuran; dichloromethane; water; acetone; toluene;
DOI:10.1039/c0ob00747a

Reference yield:

: 1274699-54-5
C₂₇H₄₃NO₅Si

: 1274699-61-4
(S)-tert-butyl 4-((1S,2R,3S)-1-(benzyloxy)-2,3-dihydroxy-4-(tosyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: ammonium fluoride-hydrogen fluoride / methanol / 18 h / 20 °C

2.1: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene / 0 °C / Inert atmosphere

3.1: osmium(VIII) oxide; citric acid / water; acetone / 20 °C

3.2: 6 h / 20 °C

4.1: 1-methyl-1H-imidazole / dichloromethane / 4 h / 0 °C / Inert atmosphere

With 1-methyl-1H-imidazole; osmium(VIII) oxide; sodium bis(2-methoxyethoxy)aluminum hydride; ammonium fluoride-hydrogen fluoride; citric acid; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene;
DOI:10.1039/c0ob00747a