Toluene-4-sulfonic acid (2R,3R)-3-benzyloxy-2-hydroxy-3-thiazol-2-yl-propyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,3R)-3-benzyloxy-2-hydroxy-3-thiazol-2-yl-propyl ester
• CAS No.: 120002-60-0
• Molecular Formula: C₂₀H₂₁NO₅S₂
• Molecular Weight: 419.522
• Mol file: 120002-60-0.mol

Synonyms:Toluene-4-sulfonic acid (2R,3R)-3-benzyloxy-2-hydroxy-3-thiazol-2-yl-propyl ester

Chemical Property of Toluene-4-sulfonic acid (2R,3R)-3-benzyloxy-2-hydroxy-3-thiazol-2-yl-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (2R,3R)-3-benzyloxy-2-hydroxy-3-thiazol-2-yl-propyl ester

There total 2 articles about Toluene-4-sulfonic acid (2R,3R)-3-benzyloxy-2-hydroxy-3-thiazol-2-yl-propyl ester 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: 36.0%

(2R,3R)-3-Benzyloxy-3-(2-thiazolyl)-1,2,3-propanetriol (119991-26-3) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (2R,3R)-3-benzyloxy-2-hydroxy-3-thiazol-2-yl-propyl ester (120002-60-0)

Guidance literature:

With triethylamine; In dichloromethane; for 24h;

DOI:10.1055/s-1988-27671

Reference yield:

(1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol (103795-11-5) → Toluene-4-sulfonic acid (2R,3R)-3-benzyloxy-2-hydroxy-3-thiazol-2-yl-propyl ester (120002-60-0)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 36 percent / Et₃N / CH₂Cl₂ / 24 h

With triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1055/s-1988-27671

Reference yield: 60.0%

Toluene-4-sulfonic acid (2R,3R)-3-benzyloxy-2-hydroxy-3-thiazol-2-yl-propyl ester (120002-60-0) → (1R,2R)-1-Benzyloxy-1-(2-thiazolyl)-1,2-propanediol (119991-31-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 0.5h; Ambient temperature;

DOI:10.1055/s-1988-27671

upstream raw materials:

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

p-toluenesulfonyl chloride

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

Downstream raw materials:

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

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