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

Base Information

• Chemical Name: (2R,3R)-2-benzyloxy-3-hydroxy-1,4-butanedioic acid dimethyl ester
• CAS No.: 104333-70-2
• Molecular Formula: C₁₃H₁₆O₆
• Molecular Weight: 268.266
• Mol file: 104333-70-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (2R,3R)-2-benzyloxy-3-hydroxy-1,4-butanedioic acid dimethyl ester 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: 96.0%

dimethyl L-tartrate (608-68-4) + benzyl bromide (100-39-0) → (2R,3R)-2-benzyloxy-3-hydroxy-1,4-butanedioic acid dimethyl ester (104333-70-2)

Guidance literature:

dimethyl L-tartrate; With tin(II) n-butoxide; In toluene; for 2h; Reflux;

benzyl bromide; With cesium fluoride; In N,N-dimethyl-formamide; for 10h;

DOI:10.1021/jo101001s

Reference yield: 31.0%

dimethyl L-tartrate (608-68-4) + benzyl bromide (100-39-0) → (2R,3R)-2-benzyloxy-3-hydroxy-1,4-butanedioic acid dimethyl ester (104333-70-2) + dimethyl 2,3-di-O-benzyl-L-tartrate (104333-84-8)

Guidance literature:

With silver(l) oxide; In 1,2-dimethoxyethane; 1.) r.t., 30 min, 2.) 55 deg C, 2 h;

DOI:10.1039/P19930001003

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → (2R,3R)-2-benzyloxy-3-hydroxy-1,4-butanedioic acid dimethyl ester (104333-70-2)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / benzene / 2 h / Reflux

2: triethylsilane; titanium tetrachloride / dichloromethane / -40 - -35 °C / Inert atmosphere

With triethylsilane; titanium tetrachloride; toluene-4-sulfonic acid; In dichloromethane; benzene;

DOI:10.1134/S1070428015070027

upstream raw materials:

dimethyl L-tartrate

benzyl bromide

iodomethylbenzene

benzaldehyde dimethyl acetal

Downstream raw materials:

(2R,3R)-2,N¹,N⁴-Tris-benzyloxy-3-hydroxy-succinamide

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

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

methyl (2R,3S)-3-(O-benzyl)-4-(O-t-butyldimethylsilyl)-2,3,4-trihydroxybutanoate