allyl 2-O-(4-methoxybenzyl)-3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside

Base Information

• Chemical Name: allyl 2-O-(4-methoxybenzyl)-3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside
• CAS No.: 914097-72-6
• Molecular Formula: C₂₄H₃₆O₈
• Molecular Weight: 452.545
• Mol file: 914097-72-6.mol

Synonyms:allyl 2-O-(4-methoxybenzyl)-3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside

Chemical Property of allyl 2-O-(4-methoxybenzyl)-3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2-O-(4-methoxybenzyl)-3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside

There total 2 articles about allyl 2-O-(4-methoxybenzyl)-3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside 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: 83.0%

allyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside (147221-63-4) + p-methoxybenzyl chloride (824-94-2) → allyl 2-O-(4-methoxybenzyl)-3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside (914097-72-6)

Guidance literature:

allyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside; With sodium hydride; In N,N-dimethyl-formamide; for 1h;

p-methoxybenzyl chloride; In N,N-dimethyl-formamide;

DOI:10.1021/ol062199b

Reference yield:

allyl β-D-galactopyranoside (2595-07-5,821794-45-0) → allyl 2-O-(4-methoxybenzyl)-3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside (914097-72-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 53 percent / p-TsOH / 16 h / 20 °C

2.1: NaH / dimethylformamide / 1 h

2.2: 83 percent / dimethylformamide

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1021/ol062199b

Reference yield:

allyl 2-O-(4-methoxybenzyl)-3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside (914097-72-6) → (2R,3R,4S,5R,6R)-6-Allyloxy-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3,4-diol

Guidance literature:

With toluene-4-sulfonic acid; In methanol;

DOI:10.1021/ol062199b

upstream raw materials:

allyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside

p-methoxybenzyl chloride

allyl β-D-galactopyranoside

Downstream raw materials:

allyl 2-O- (4-methoxylbenzyl)-3,4,6-O-triacetyl-β-D-galactopyranoside

3,4,6-tri-O-acetyl-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl trichloroacetimidate

allyl 2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside

2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-trichloroacetimide