(2R,3R,4S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3,4-diol

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3,4-diol
• CAS No.: 53685-11-3
• Molecular Formula: C₂₁H₂₆O₆
• Molecular Weight: 374.434
• Mol file: 53685-11-3.mol

Synonyms:(2R,3R,4S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3,4-diol

Chemical Property of (2R,3R,4S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3,4-diol

There total 32 articles about (2R,3R,4S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3,4-diol 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: 91.0%

methyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside (102854-30-8) → methyl 2,6-di-O-benzyl-β-D-galactopyranoside (53685-11-3,58341-66-5,86342-20-3,95015-48-8,100662-78-0,51842-27-4)

Guidance literature:

With acetic acid; In water; at 70 ℃; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.tetlet.2017.04.056

Reference yield: 88.0%

benzyl bromide (100-39-0) + methyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-α-D-lyxo-hexopyranosyl-2-ulose (145933-55-7) → methyl 2,6-di-O-benzyl-α-D-talopyranoside (922520-71-6) + (2R,3R,4S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3,4-diol (53685-11-3)

Guidance literature:

Multistep reaction;

DOI:10.1002/ejoc.200600526

Reference yield: 72.0%

benzyl bromide (100-39-0) + methyl beta-D-glucopyranoside (709-50-2) → methyl β-D-glucopyranoside 2,6-dibenzyl ether (51842-27-4,53685-11-3,58341-66-5,86342-20-3,95015-48-8,100662-78-0)

Guidance literature:

methyl beta-D-glucopyranoside; With di(n-butyl)tin oxide; In toluene; for 1h; Reflux; Inert atmosphere;

benzyl bromide; With tetrabutylammomium bromide; In toluene; at 100 ℃; for 10h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2013.02.024

upstream raw materials:

methyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside

benzyl chloride

methyl beta-D-galactopyranoside

benzyl bromide

Downstream raw materials:

methyl 2,3,4,6-tetra-O-benzyl α-D-galactopyranoside

methyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside

methyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside

Methyl-2,6-di-O-benzyl-3,4-O-(1-ethoxyethyliden)-β-D-galactopyranosid