(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
• Mol file: 1274699-61-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

(S)-tert-butyl 4-((1S,2R,3S)-1-(benzyloxy)-2,3,4-trihydroxybutyl)-2,2-dimethyloxazolidine-3-carboxylate (1274699-59-0) + p-toluenesulfonyl chloride (98-59-9) → (S)-tert-butyl 4-((1S,2R,3S)-1-(benzyloxy)-2,3-dihydroxy-4-(tosyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate (1274699-61-4)

Guidance literature:

With 1-methyl-1H-imidazole; In dichloromethane; at 0 ℃; for 4h; Inert atmosphere;

DOI:10.1039/c0ob00747a

Reference yield:

(S)-tert-butyl 4-((R)-1-(benzyloxy)-4-hydroxybut-2-yn-1-yl)-2,2-dimethyloxazolidine-3-carboxylate (1274699-53-4) → (S)-tert-butyl 4-((1S,2R,3S)-1-(benzyloxy)-2,3-dihydroxy-4-(tosyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate (1274699-61-4)

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:

C27H43NO5Si (1274699-54-5) → (S)-tert-butyl 4-((1S,2R,3S)-1-(benzyloxy)-2,3-dihydroxy-4-(tosyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate (1274699-61-4)

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

upstream raw materials:

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

p-toluenesulfonyl chloride

C₂₇H₄₃NO₅Si

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

Downstream raw materials:

(2S,3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-ium chloride

C₂₀H₂₇NO₇S

(3S,4R,5S,6S)-5-(benzyloxy)-6-(hydroxymethyl)piperidine-3,4-diol