(2S,3R)-3-(N-Boc-amino)-1-oxirane-4-phenylbutane

Base Information

• Chemical Name: (2S,3R)-3-(N-Boc-amino)-1-oxirane-4-phenylbutane
• CAS No.: 156474-22-5
• Molecular Formula: C15H21 N O3
• Molecular Weight: 263.337
• Mol file: 156474-22-5.mol

Synonyms:Carbamicacid, (1-oxiranyl-2-phenylethyl)-, 1,1-dimethylethyl ester, [S-(R*,S*)]-;Carbamic acid, [(1R)-1-(2S)-oxiranyl-2-phenylethyl]-, 1,1-dimethylethyl ester(9CI); (2S,3R)-3-(tert-Butoxycarbonylamino)-1,2-epoxy-4-phenylbutane

Chemical Property of (2S,3R)-3-(N-Boc-amino)-1-oxirane-4-phenylbutane

Chemical Property:

• PSA: 54.35000
• LogP: 2.72560
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, DMSO, Methanol

Purity/Quality:

99.0% ^*data from raw suppliers

Carbamicacid,N-[(1R)-1-[(2S)-2-oxiranyl]-2-phenylethyl]-,1,1-dimethylethylester 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S,3R)-3-(tert-Butoxycarbonylamino)-1,2-epoxy-4-phenylbutane is an intermediate in the synthesis of Atazanavir (A790050), a novel azapeptide HIV protease inhibitor used as an antiviral agent.

Technology Process of (2S,3R)-3-(N-Boc-amino)-1-oxirane-4-phenylbutane

There total 3 articles about (2S,3R)-3-(N-Boc-amino)-1-oxirane-4-phenylbutane 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: 88.0%

(R)-N-(tert-butoxycarbonyl)-3-amino-4-phenyl-1-butene (244092-76-0) → tert-butyl [(2R,3S)]-(-)-(1-oxiranyl-2-phenylethyl)carbamate (156474-22-5)

Guidance literature:

With 2,6-dichloropyridine N-oxide; ruthenium porphyrins on a styrene-divinylbenzene copolymer; In benzene; at 40 ℃; for 48h;

DOI:10.1021/ja000461k

Reference yield:

(R)-N-(tert-butoxycarbonyl)-3-amino-4-phenyl-1-butene (244092-76-0) → tert-butyl [(2R,3S)]-(-)-(1-oxiranyl-2-phenylethyl)carbamate (156474-22-5) + tert-butyl [(2R,3R)]-(-)-(1-oxiranyl-2-phenylethyl)carbamate (156474-21-4)

Guidance literature:

With Oxone; ammonium acetate; ammonium bicarbonate; chloro(meso-tetrakis(2,6-dichlorophenyl)porphyrinato)manganese(III); In water; acetonitrile; at 20 ℃; for 1h; Product distribution / selectivity;

Reference yield:

→ tert-butyl [(2R,3S)]-(-)-(1-oxiranyl-2-phenylethyl)carbamate (156474-22-5)

Guidance literature:

upstream raw materials:

(R)-N-(tert-butoxycarbonyl)-3-amino-4-phenyl-1-butene

Downstream raw materials:

((1R,2R)-1-Benzyl-3-benzylamino-2-hydroxy-propyl)-carbamic acid tert-butyl ester

((1R,2R)-1-Benzyl-2-hydroxy-3-methylamino-propyl)-carbamic acid tert-butyl ester

((1R,2R)-1-Benzyl-2-hydroxy-3-isopropylamino-propyl)-carbamic acid tert-butyl ester

((1R,2R)-1-Benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid tert-butyl ester