(2R,3R)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-diol cyclic sulfate

Base Information

• Chemical Name: (2R,3R)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-diol cyclic sulfate
• CAS No.: 151359-20-5
• Molecular Formula: C₁₇H₂₈O₆SSi
• Molecular Weight: 388.557
• Mol file: 151359-20-5.mol

Synonyms:(2R,3R)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-diol cyclic sulfate

Chemical Property of (2R,3R)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-diol cyclic sulfate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-diol cyclic sulfate

There total 4 articles about (2R,3R)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-diol cyclic sulfate 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:

((4R,5R)-5-Benzyloxymethyl-2-oxo-2λ4-[1,3,2]dioxathiolan-4-ylmethoxy)-tert-butyl-dimethyl-silane (1027578-88-6) → (2R,3R)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-diol cyclic sulfate (151359-20-5)

Guidance literature:

With ruthenium trichloride; sodium periodate; Yield given;

DOI:10.1016/S0040-4039(00)60654-8

Reference yield:

1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-diol → (2R,3R)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-diol cyclic sulfate (151359-20-5)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N, SOCl₂ / CH₂Cl₂ / 0.17 h

2: NaIO₄, RuCl₃*3H₂O / CCl₄; acetonitrile; H₂O / 1 h / 0 °C

With ruthenium trichloride; sodium periodate; thionyl chloride; triethylamine; In tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1021/jo00088a045

Reference yield:

(2R,3R)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-diol (151435-00-6) → (2R,3R)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-diol cyclic sulfate (151359-20-5)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂

2: RuCl₃, NaIO₄

With ruthenium trichloride; sodium periodate; thionyl chloride;

DOI:10.1016/S0040-4039(00)60654-8

upstream raw materials:

((4R,5R)-5-Benzyloxymethyl-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-ylmethoxy)-tert-butyl-dimethyl-silane

(E)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>-2-butene

(2R,3R)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-diol

Downstream raw materials:

(2R,3S)-1-(Benzyloxy)-2,3-butanediol

(2R,3S)-1-(Benzyloxy)-2,3-octanediol

(2R,3R)-1-(Benzyloxy)-4-(phenylthio)-2,3-butanediol

(2R,3R)-1-(Benzyloxy)-4-iodo-2,3-butanediol