benzyl (2S,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxylate

Base Information

• Chemical Name: benzyl (2S,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxylate
• CAS No.: 499140-11-3
• Molecular Formula: C₁₇H₁₇NO₄S
• Molecular Weight: 331.392
• Mol file: 499140-11-3.mol

Synonyms:benzyl (2S,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxylate

Chemical Property of benzyl (2S,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxylate

There total 3 articles about benzyl (2S,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxylate 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: 62.0%

(1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol (104863-92-5) → benzyl (2S,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxylate (499140-11-3) + benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate (499140-12-4)

Guidance literature:

With dmap; thionyl chloride; In dichloromethane; at -40 ℃;

DOI:10.1021/ol027232i

Reference yield:

(1R,2S)-norephedrine (492-41-1,58550-13-3,757124-50-8) → benzyl (2S,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxylate (499140-11-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 0.08 h / 0 °C

2: 44 percent / thionyl chloride; 2,6-lutidine / CH₂Cl₂ / 0.25 h / -40 °C

With 2,6-dimethylpyridine; dmap; thionyl chloride; In dichloromethane;

DOI:10.1021/ol027232i

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → benzyl (2S,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxylate (499140-11-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 0.08 h / 0 °C

2: 44 percent / thionyl chloride; 2,6-lutidine / CH₂Cl₂ / 0.25 h / -40 °C

With 2,6-dimethylpyridine; dmap; thionyl chloride; In dichloromethane;

DOI:10.1021/ol027232i

upstream raw materials:

(1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol

(1R,2S)-norephedrine

benzyl chloroformate

Downstream raw materials:

diethyl sulphide

dimethyl sulfoxide

1,1'-sulfinylbisbenzene

(1R,2S)-2-{[(benzyloxy)carbonyl]amino}-1-phenylpropyl (S)-benzenesulfinate