(2R,3R)-3-azido-2-tert-butyldimethylsiloxy-3-phenyl-1-p-toluenesulfonyloxypropane

Base Information

• Chemical Name: (2R,3R)-3-azido-2-tert-butyldimethylsiloxy-3-phenyl-1-p-toluenesulfonyloxypropane
• CAS No.: 146499-47-0
• Molecular Formula: C₂₂H₃₁N₃O₄SSi
• Molecular Weight: 461.657

Synonyms:(2R,3R)-3-azido-2-tert-butyldimethylsiloxy-3-phenyl-1-p-toluenesulfonyloxypropane

Chemical Property of (2R,3R)-3-azido-2-tert-butyldimethylsiloxy-3-phenyl-1-p-toluenesulfonyloxypropane

Chemical Property:

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Technology Process of (2R,3R)-3-azido-2-tert-butyldimethylsiloxy-3-phenyl-1-p-toluenesulfonyloxypropane

There total 4 articles about (2R,3R)-3-azido-2-tert-butyldimethylsiloxy-3-phenyl-1-p-toluenesulfonyloxypropane 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:

(2R,3R)-3-azido-3-phenyl-propane-1,2diol (121745-57-1) → (2R,3R)-3-azido-2-tert-butyldimethylsiloxy-3-phenyl-1-p-toluenesulfonyloxypropane (146499-47-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 398 mg / Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

2: imidazole / dimethylformamide / 19 h / Ambient temperature

With 1H-imidazole; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)80749-3

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) + Toluene-4-sulfonic acid (2R,3R)-3-azido-2-hydroxy-3-phenyl-propyl ester (156350-20-8) → (2R,3R)-3-azido-2-tert-butyldimethylsiloxy-3-phenyl-1-p-toluenesulfonyloxypropane (146499-47-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 19h; Ambient temperature;

DOI:10.1016/S0040-4039(00)74779-4

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → (2R,3R)-3-azido-2-tert-butyldimethylsiloxy-3-phenyl-1-p-toluenesulfonyloxypropane (146499-47-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 398 mg / Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

2: imidazole / dimethylformamide / 19 h / Ambient temperature

With 1H-imidazole; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)80749-3

upstream raw materials:

tert-butyldimethylsilyl chloride

Toluene-4-sulfonic acid (2R,3R)-3-azido-2-hydroxy-3-phenyl-propyl ester

(2R,3R)-3-azido-3-phenyl-propane-1,2diol

p-toluenesulfonyl chloride

Downstream raw materials:

Toluene-4-sulfonic acid (2R,3R)-3-amino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propyl ester

(2R,3S)-N-p-toluenesulfonyl-3-hydroxy-2-phenylazetidine

(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-azetidine-2-carboxylic acid

(2R,3S)-N-p-toluenesulfonyl-3-tert-butyldimethylsiloxy-2-phenylazetidine

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