isopropyl (2R,3S)-3-(acetylamino)-2-(methanesulfonyloxy)-3-phenylpropionate

Base Information

• Chemical Name: isopropyl (2R,3S)-3-(acetylamino)-2-(methanesulfonyloxy)-3-phenylpropionate
• CAS No.: 274681-81-1
• Molecular Formula: C₁₅H₂₁NO₆S
• Molecular Weight: 343.401
• Mol file: 274681-81-1.mol

Synonyms:isopropyl (2R,3S)-3-(acetylamino)-2-(methanesulfonyloxy)-3-phenylpropionate

Chemical Property of isopropyl (2R,3S)-3-(acetylamino)-2-(methanesulfonyloxy)-3-phenylpropionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of isopropyl (2R,3S)-3-(acetylamino)-2-(methanesulfonyloxy)-3-phenylpropionate

There total 3 articles about isopropyl (2R,3S)-3-(acetylamino)-2-(methanesulfonyloxy)-3-phenylpropionate 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%

methanesulfonyl chloride (124-63-0) + (2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester (195624-97-6) → isopropyl (2R,3S)-3-(acetylamino)-2-(methanesulfonyloxy)-3-phenylpropionate (274681-81-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1016/S0040-4020(01)00090-4

Reference yield:

(E)-isopropyl cinnamate (60512-85-8) → isopropyl (2R,3S)-3-(acetylamino)-2-(methanesulfonyloxy)-3-phenylpropionate (274681-81-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / LiOH; (DHQ)2-PHAL / K₂Os₂O₂(OH)4

2: 93 percent / Et₃N / CH₂Cl₂ / 3 h / 0 - 20 °C

With lithium hydroxide; (DHQ)2-PHAL; triethylamine; potassium osmate; In dichloromethane; 1: Sharpless asymmetric aminohydroxylation / 2: Mesylation;

DOI:10.1021/ol005681h

Reference yield:

isopropyl cinnamate (7780-06-5) → isopropyl (2R,3S)-3-(acetylamino)-2-(methanesulfonyloxy)-3-phenylpropionate (274681-81-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / K₂OsO₂(OH)4; (DHQ)2-PHAL

2: 93 percent / Et₃N / CH₂Cl₂ / 3 h / 0 - 20 °C

With potassium dioxotetrahydroxoosmate(VI); (DHQ)2-PHAL; triethylamine; In dichloromethane; 1: Sharpless aminohydroxylation;

DOI:10.1016/S0040-4020(01)00090-4

upstream raw materials:

methanesulfonyl chloride

(2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester

isopropyl cinnamate

(E)-isopropyl cinnamate

Downstream raw materials:

(4S,5S)-5-(isopropoxycarbonyl)-2-methyl-4-phenyl-2-oxazoline

(4S,5R)-5-(isopropoxycarbonyl)-2-methyl-4-phenyl-2-oxazoline

2-azido-3-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

methyl (2R,3S)-2-amino-3-(tert-butoxycarbonylamino)-3-phenylpropionate