methyl[2R-(R*,R*)]-2-hydroxy-4-oxo-3-phenylmethoxy-4-[(phenylmethoxy)-amino]-butanoate

Base Information

• Chemical Name: methyl[2R-(R*,R*)]-2-hydroxy-4-oxo-3-phenylmethoxy-4-[(phenylmethoxy)-amino]-butanoate
• CAS No.: 104333-72-4
• Molecular Formula: C₁₉H₂₁NO₆
• Molecular Weight: 359.379
• Mol file: 104333-72-4.mol

Synonyms:methyl[2R-(R*,R*)]-2-hydroxy-4-oxo-3-phenylmethoxy-4-[(phenylmethoxy)-amino]-butanoate

Chemical Property of methyl[2R-(R*,R*)]-2-hydroxy-4-oxo-3-phenylmethoxy-4-[(phenylmethoxy)-amino]-butanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl[2R-(R*,R*)]-2-hydroxy-4-oxo-3-phenylmethoxy-4-[(phenylmethoxy)-amino]-butanoate

There total 3 articles about methyl[2R-(R*,R*)]-2-hydroxy-4-oxo-3-phenylmethoxy-4-[(phenylmethoxy)-amino]-butanoate 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%

O-benzylhydoxylamine hydrochloride (2687-43-6) + (2R,3R)-2-Benzyloxy-3-hydroxy-succinic acid 4-methyl ester (104333-71-3) → methyl[2R-(R*,R*)]-2-hydroxy-4-oxo-3-phenylmethoxy-4-[(phenylmethoxy)-amino]-butanoate (104333-72-4)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; water; for 0.5h;

DOI:10.1016/S0040-4020(01)81921-9

Reference yield:

dimethyl 2,3-O-benzylidene-L-tartrate (38270-72-3) → methyl[2R-(R*,R*)]-2-hydroxy-4-oxo-3-phenylmethoxy-4-[(phenylmethoxy)-amino]-butanoate (104333-72-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / NaCNBH₃, HCl / acetonitrile; diethyl ether / 2 h / Ambient temperature

2: 1.) K₂CO₃; 2.) 1-ethyl-3-(dimethylamino)propylcarbodiimide hydrochloride, HCl / 1.) dioxane-water, r.t., 5 h; 2.) water, 30 min

With hydrogenchloride; sodium cyanoborohydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In diethyl ether; acetonitrile;

DOI:10.1016/S0040-4020(01)81921-9

Reference yield:

O-benzylhydoxylamine hydrochloride (2687-43-6) + (2R,3R)-2-benzyloxy-3-hydroxy-1,4-butanedioic acid dimethyl ester (104333-70-2) → (2R,3R)-2,N1,N4-Tris-benzyloxy-3-hydroxy-succinamide (104211-09-8) + methyl[2R-(R*,R*)]-2-hydroxy-4-oxo-3-phenylmethoxy-4-[(phenylmethoxy)-amino]-butanoate (104333-72-4) + (2R,3R)-2,N-Bis-benzyloxy-3-hydroxy-succinamic acid methyl ester

Guidance literature:

With hydrogenchloride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; Yield given. Multistep reaction. Yields of byproduct given; 1.) dioxane-water, r.t., 5 h; 2.) water, 30 min;

DOI:10.1016/S0040-4020(01)81921-9

upstream raw materials:

O-benzylhydoxylamine hydrochloride

(2R,3R)-2-benzyloxy-3-hydroxy-1,4-butanedioic acid dimethyl ester

(2R,3R)-2-Benzyloxy-3-hydroxy-succinic acid 4-methyl ester

dimethyl 2,3-O-benzylidene-L-tartrate

Downstream raw materials:

Methyl(2S-trans)-1,3-bis-(phenylmethoxy)-4-oxo-2-azetidine-carboxylate

methyl[2R-(R*,R*)]-2-[(4-methylphenylsulfonyl)-oxy]-4-oxo-3-benzyloxy-4-[benzyloxy-amino]-butanoate