(2S,4S,5R)-2-Oxo-4,5-diphenyl-2λ⁴-[1,2,3]oxathiazolidine-3-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,4S,5R)-2-Oxo-4,5-diphenyl-2λ⁴-[1,2,3]oxathiazolidine-3-carboxylic acid benzyl ester
• CAS No.: 813459-67-5
• Molecular Formula: C₂₂H₁₉NO₄S
• Molecular Weight: 393.463

Synonyms:(2S,4S,5R)-2-Oxo-4,5-diphenyl-2λ⁴-[1,2,3]oxathiazolidine-3-carboxylic acid benzyl ester

Chemical Property of (2S,4S,5R)-2-Oxo-4,5-diphenyl-2λ⁴-[1,2,3]oxathiazolidine-3-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (2S,4S,5R)-2-Oxo-4,5-diphenyl-2λ⁴-[1,2,3]oxathiazolidine-3-carboxylic acid benzyl ester

There total 3 articles about (2S,4S,5R)-2-Oxo-4,5-diphenyl-2λ⁴-[1,2,3]oxathiazolidine-3-carboxylic acid benzyl 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:

benzyl ((1S,2R)-2-hydroxy-1,2-diphenylethyl)carbamate (813459-61-9) → (2S,4S,5R)-2-Oxo-4,5-diphenyl-2λ4-[1,2,3]oxathiazolidine-3-carboxylic acid benzyl ester (813459-67-5) + (2R,4S,5R)-2-Oxo-4,5-diphenyl-2λ4-[1,2,3]oxathiazolidine-3-carboxylic acid benzyl ester

Guidance literature:

With dmap; sulfuryl dichloride; In dichloromethane; at -45 ℃; for 1h;

DOI:10.1021/jo048576k

Reference yield:

(1R,2S)-2-Amino-1,2-diphenylethanol (23190-16-1) → (2S,4S,5R)-2-Oxo-4,5-diphenyl-2λ4-[1,2,3]oxathiazolidine-3-carboxylic acid benzyl ester (813459-67-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 3 h / 0 °C

2: SO₂Cl₂; 2,4,6-collidine / CH₂Cl₂ / 1 h / -45 °C

With 2,4,6-trimethyl-pyridine; sulfuryl dichloride; sodium carbonate; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo048576k

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (2S,4S,5R)-2-Oxo-4,5-diphenyl-2λ4-[1,2,3]oxathiazolidine-3-carboxylic acid benzyl ester (813459-67-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 3 h / 0 °C

2: SO₂Cl₂; 2,4,6-collidine / CH₂Cl₂ / 1 h / -45 °C

With 2,4,6-trimethyl-pyridine; sulfuryl dichloride; sodium carbonate; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo048576k

upstream raw materials:

benzyl ((1S,2R)-2-hydroxy-1,2-diphenylethyl)carbamate

(1R,2S)-2-Amino-1,2-diphenylethanol

benzyl chloroformate

Downstream raw materials:

(4S,5R)-3-((S)-2-Methyl-propane-2-sulfinyl)-4,5-diphenyl-oxazolidin-2-one

(4S,5R)-4,5-diphenyl-1,3-oxazolidin-2-one

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