(2R)-(3S)-(4S)-2,3-O-isopropylidene-4-O-benzyloxymethoxyarabinonic acid methyl ester

Base Information

• Chemical Name: (2R)-(3S)-(4S)-2,3-O-isopropylidene-4-O-benzyloxymethoxyarabinonic acid methyl ester
• CAS No.: 116525-13-4
• Molecular Formula: C₁₇H₂₄O₆
• Molecular Weight: 324.374
• Mol file: 116525-13-4.mol

Synonyms:

Chemical Property of (2R)-(3S)-(4S)-2,3-O-isopropylidene-4-O-benzyloxymethoxyarabinonic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-(3S)-(4S)-2,3-O-isopropylidene-4-O-benzyloxymethoxyarabinonic acid methyl ester

There total 2 articles about (2R)-(3S)-(4S)-2,3-O-isopropylidene-4-O-benzyloxymethoxyarabinonic acid methyl 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:

(S)-(benzyloxymethoxy)propanal (63296-56-0) → (2R)-(3S)-(4S)-2,3-O-isopropylidene-4-O-benzyloxymethoxyarabinonic acid methyl ester (116525-13-4)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / Ambient temperature

2: 1.) osmium tetraoxide, trimethylamine-N-oxide dihydrate; 2.) toluene-4-sulfonic acid, CuSO₄ / 1.) t-butanol, acetone, water, room temp., 12 h; 2.) acetone, room temp.

With osmium(VIII) oxide; trimethylamine-N-oxide; toluene-4-sulfonic acid; copper(II) sulfate; In dichloromethane;

DOI:10.1016/S0040-4020(01)85840-3

Reference yield:

(E)-(4S)-4-benzyloxymethoxypent-2-enoic acid methyl ester (116490-93-8) → (2S)-(3R)-(4S)-2,3-O-isopropylidene-4-O-benzyloxymethoxyxylonic acid methyl ester (116491-06-6) + (2R)-(3S)-(4S)-2,3-O-isopropylidene-4-O-benzyloxymethoxyarabinonic acid methyl ester (116525-13-4)

Guidance literature:

With osmium(VIII) oxide; trimethylamine-N-oxide; toluene-4-sulfonic acid; copper(II) sulfate; Multistep reaction; 1.) t-butanol, acetone, water, room temp., 12 h; 2.) acetone, room temp.;

DOI:10.1016/S0040-4020(01)85840-3

upstream raw materials:

(E)-(4S)-4-benzyloxymethoxypent-2-enoic acid methyl ester

(S)-(benzyloxymethoxy)propanal