(1R,2R)-1-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-thiazol-2-yl-propan-2-ol

Base Information

• Chemical Name: (1R,2R)-1-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-thiazol-2-yl-propan-2-ol
• CAS No.: 119991-41-2
• Molecular Formula: C₁₉H₂₉NO₃SSi
• Molecular Weight: 379.596

Synonyms:(1R,2R)-1-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-thiazol-2-yl-propan-2-ol

Chemical Property of (1R,2R)-1-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-thiazol-2-yl-propan-2-ol

Chemical Property:

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Technology Process of (1R,2R)-1-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-thiazol-2-yl-propan-2-ol

There total 2 articles about (1R,2R)-1-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-thiazol-2-yl-propan-2-ol 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: 84.0%

(2R,3R)-3-Benzyloxy-3-(2-thiazolyl)-1,2,3-propanetriol (119991-26-3) + tert-butyldimethylsilyl chloride (18162-48-6) → (1R,2R)-1-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-thiazol-2-yl-propan-2-ol (119991-41-2)

Guidance literature:

With 1H-imidazole; In dichloromethane; for 4h;

DOI:10.1055/s-1988-27671

Reference yield:

(1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol (103795-11-5) → (1R,2R)-1-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-thiazol-2-yl-propan-2-ol (119991-41-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / aq. CF₃CO₂H / 0.25 h / Ambient temperature

2: 84 percent / imidazole / CH₂Cl₂ / 4 h

With 1H-imidazole; trifluoroacetic acid; In dichloromethane;

DOI:10.1055/s-1988-27671

Reference yield: 98.0%

methanesulfonyl chloride (124-63-0) + (1R,2R)-1-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-thiazol-2-yl-propan-2-ol (119991-41-2) → (2R,3R)-3-Benzyloxy-1-tert-butyldimethylsilyloxy-2-methylsulfonyloxy-3-(2-thiazolyl)-1,2,3-propanetriol (119991-27-4)

Guidance literature:

With triethylamine; In dichloromethane; for 2h;

DOI:10.1055/s-1988-27671

upstream raw materials:

(2R,3R)-3-Benzyloxy-3-(2-thiazolyl)-1,2,3-propanetriol

tert-butyldimethylsilyl chloride

(1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol

Downstream raw materials:

(2R,3R)-3-Benzyloxy-1-tert-butyldimethylsilyloxy-2-methylsulfonyloxy-3-(2-thiazolyl)-1,2,3-propanetriol

(2S,3R)-1,3-Dibenzyloxy-3-(2-thiazolyl)-1,2,3-propanetriol

Methanesulfonic acid (1R,2R)-2-benzyloxy-1-hydroxymethyl-2-thiazol-2-yl-ethyl ester

(1R,2S)-1-Benzyloxy-1-(2-thiazolyl)-1,2-propanediol

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