methyl (2S,3S)-2-amino-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate

Base Information

• Chemical Name: methyl (2S,3S)-2-amino-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate
• CAS No.: 188446-25-5
• Molecular Formula: C₁₇H₁₉NO₄
• Molecular Weight: 301.342
• Mol file: 188446-25-5.mol

Synonyms:methyl (2S,3S)-2-amino-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate

Chemical Property of methyl (2S,3S)-2-amino-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,3S)-2-amino-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate

There total 4 articles about methyl (2S,3S)-2-amino-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate 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: 48.0%

(2R,5S,αS)-5-[4'-benzyloxy-α-hydroxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (188446-23-3) → methyl (2S,3S)-2-amino-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate (188446-25-5)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; acetonitrile; at 20 ℃; for 22h; Inert atmosphere;

DOI:10.1002/chem.201701259

Reference yield:

methyl 2-amino-3-(4-benzyloxyphenyl)-3-oxopropionate hydrochloride → (2R,3R)-2-Amino-3-(4-benzyloxy-phenyl)-3-hydroxy-propionic acid methyl ester + methyl (2S,3S)-2-amino-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate (188446-25-5)

Guidance literature:

With hydrogen; sodium acetate; acetic acid; Ir-(S)-MeO-BIPHEP-BARF; at 23 ℃; for 96h; under 3420 Torr; Title compound not separated from byproducts;

DOI:10.1021/ol061796v

Reference yield:

p-benzyloxybenzaldehyde (4397-53-9) → methyl (2S,3S)-2-amino-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate (188446-25-5)

Guidance literature:

Multi-step reaction with 2 steps

1: n-BuLi / tetrahydrofuran / 1.5 h / -78 - -30 °C

2: 1.) 0.25N HCl, 2.) NaHCO₃ / 2.) H₂O

With hydrogenchloride; n-butyllithium; sodium hydrogencarbonate; In tetrahydrofuran;

DOI:10.1021/jo961346o

upstream raw materials:

(2R,5S,αS)-5-[4'-benzyloxy-α-hydroxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine

p-benzyloxybenzaldehyde

Downstream raw materials:

(2S,3S)-2-Amino-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester

methyl (2S,3S)-2-amino-3-(4-(benzyloxy)phenyl)-3-((tert-butyldimethylsilyl)oxy)propanoate