(2R)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate)

Base Information

• Chemical Name: (2R)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate)
• CAS No.: 253776-35-1
• Molecular Formula: C₁₂H₁₂F₆O₇S₂
• Molecular Weight: 446.345
• Mol file: 253776-35-1.mol

Synonyms:(2R)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate)

Chemical Property of (2R)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate)

There total 1 articles about (2R)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate) 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: 93.0%

trifluoromethylsulfonic anhydride (358-23-6) + (2S)-3-(benzyloxy)propane-1,2-diol (17325-85-8) → (2R)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate) (253776-35-1)

Guidance literature:

With pyridine; In dichloromethane; at -30 ℃; for 0.333333h;

DOI:10.1021/jo991052d

Reference yield: 89.0%

(2R)-1-[(tert-butyldimethylsilyl)oxy]-2-[(tert-butyloxycarbonyl)amino]-3-(phenylsulfonyl)propane (187409-49-0) + (2R)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate) (253776-35-1) → (2R,3S,5R)-1-tert-butoxycarbonyl-2-tert-butyldimethylsilyloxymethyl-3-phenylsulfonyl-5-benzyloxymethylpyrrolidine (253776-47-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -70 ℃; for 1h;

DOI:10.1021/jo991052d

Reference yield:

(2R)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate) (253776-35-1) → (2R,5R)-1-tert-butoxycarbonyl-2-tert-butyldimethylsilyloxymethyl-5-benzyloxymethylpyrrolidine (253776-48-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / BuLi / tetrahydrofuran / 1 h / -70 °C

2: 78 percent / Na-Hg; Na₂HPO₄ / methanol / 0 - 20 °C

With disodium hydrogenphosphate; n-butyllithium; sodium amalgam; In tetrahydrofuran; methanol; 1: Cyclization / 2: Reduction;

DOI:10.1021/jo991052d

upstream raw materials:

trifluoromethylsulfonic anhydride

(2S)-3-(benzyloxy)propane-1,2-diol

Downstream raw materials:

(2R,3S,5R)-1-tert-butoxycarbonyl-2-tert-butyldimethylsilyloxymethyl-3-phenylsulfonyl-5-benzyloxymethylpyrrolidine

(2R,5R)-1-tert-butoxycarbonyl-2-tert-butyldimethylsilyloxymethyl-5-benzyloxymethylpyrrolidine