(Z)-methyl 2-((benzyloxycarbonyl)amino)-3-(3-hydroxyphenyl)acrylate

Base Information

• Chemical Name: (Z)-methyl 2-((benzyloxycarbonyl)amino)-3-(3-hydroxyphenyl)acrylate
• CAS No.: 234122-56-6
• Molecular Formula: C₁₈H₁₇NO₅
• Molecular Weight: 327.337
• Mol file: 234122-56-6.mol

Synonyms:(Z)-methyl 2-((benzyloxycarbonyl)amino)-3-(3-hydroxyphenyl)acrylate

Chemical Property of (Z)-methyl 2-((benzyloxycarbonyl)amino)-3-(3-hydroxyphenyl)acrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-methyl 2-((benzyloxycarbonyl)amino)-3-(3-hydroxyphenyl)acrylate

There total 1 articles about (Z)-methyl 2-((benzyloxycarbonyl)amino)-3-(3-hydroxyphenyl)acrylate 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: 90.0%

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0) + meta-hydroxybenzaldehyde (100-83-4) → (Z)-methyl 2-((benzyloxycarbonyl)amino)-3-(3-hydroxyphenyl)acrylate (234122-56-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 25 ℃; for 2h;

Reference yield: 90.0%

(Z)-methyl 2-((benzyloxycarbonyl)amino)-3-(3-hydroxyphenyl)acrylate (234122-56-6) → (S)-methyl 2-((benzyloxycarbonyl)amino)-3-(3-hydroxyphenyl)propanoate (234122-64-6)

Guidance literature:

With hydrogen; <(S,S)-Et-DuP-Rh>(+)TfO(-); for 96h; under 3102.89 Torr;

Reference yield:

(Z)-methyl 2-((benzyloxycarbonyl)amino)-3-(3-hydroxyphenyl)acrylate (234122-56-6) → methyl (S)-2-amino-3-(3-hydroxyphenyl)propanoate (167935-97-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / H₂ / [(S,S)-Et-DuP-Rh]⁺TfO^- / methanol / 96 h / 3102.97 Torr

2: 96 percent / H₂ / Pd/C / methanol / 12 h / 25 °C / 760.05 Torr

With hydrogen; palladium on activated charcoal; (+)-1,2-bis((2S,5S)-2,5-diethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; In methanol; 1: stereoselective hydrogenation / 2: Hydrogenolysis;

DOI:10.1021/ja994285v

upstream raw materials:

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

meta-hydroxybenzaldehyde

Downstream raw materials:

(S)-methyl 2-((benzyloxycarbonyl)amino)-3-(3-hydroxyphenyl)propanoate

methyl (S)-2-amino-3-(3-hydroxyphenyl)propanoate

(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionic acid methyl ester

(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionic acid