(+)-(2R,3S)-isopropyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate

Base Information

• Chemical Name: (+)-(2R,3S)-isopropyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate
• CAS No.: 888716-49-2
• Molecular Formula: C₂₀H₂₃NO₅
• Molecular Weight: 357.406
• Mol file: 888716-49-2.mol

Synonyms:(+)-(2R,3S)-isopropyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate

Chemical Property of (+)-(2R,3S)-isopropyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2R,3S)-isopropyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate

There total 6 articles about (+)-(2R,3S)-isopropyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate 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:

(E)-isopropyl cinnamate (60512-85-8) + benzyloxycarbonylamino-4-chlorobenzoate (1262306-22-8) → (+)-(2R,3S)-isopropyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate (888716-49-2) + (+)-isopropyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate + (-)-isopropyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate

Guidance literature:

benzyloxycarbonylamino-4-chlorobenzoate; With osmium(VIII) oxide; hydroquinidein 1,4-phthalazinediyl diether; In acetonitrile; at 20 ℃; for 0.166667h;

(E)-isopropyl cinnamate; In water; acetonitrile; at 20 ℃; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/jo1018816

Reference yield:

(E)-isopropyl cinnamate (60512-85-8) + benzyloxycarbonylamino-4-chlorobenzoate (1262306-22-8) → (+)-(2R,3S)-isopropyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate (888716-49-2) + (-)-(2S,3R)-isopropyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate (1054314-37-2) + (+)-isopropyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate + (-)-isopropyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate

Guidance literature:

benzyloxycarbonylamino-4-chlorobenzoate; With osmium(VIII) oxide; hydroquinine (anthraquinone-1,4-diyl) diether; In acetonitrile; at 20 ℃; for 0.166667h;

(E)-isopropyl cinnamate; In water; acetonitrile; at 20 ℃; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/jo1018816

Reference yield:

Benzyl N-hydroxycarbamate (3426-71-9) → (+)-(2R,3S)-isopropyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate (888716-49-2) + (+)-isopropyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate + (-)-isopropyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / diethyl ether / 0 - 20 °C

2.1: osmium(VIII) oxide; hydroquinidein 1,4-phthalazinediyl diether / acetonitrile / 0.17 h / 20 °C

2.2: 20 °C

With osmium(VIII) oxide; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; In diethyl ether; acetonitrile;

DOI:10.1021/jo1018816

upstream raw materials:

Benzyl N-hydroxycarbamate

(E)-isopropyl cinnamate

benzyloxycarbonylamino-4-chlorobenzoate

benzyl chloroformate

Downstream raw materials:

C₁₀H₉NO₄

(-)-(4S,5R)-methyl 2-oxo-4-phenyloxazolidine-5-carboxylate

(1S,2S)-2-amino-1-phenyl-1,3-propanediol