phenyl 3-O-allyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 3-O-allyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside
• CAS No.: 556039-05-5
• Molecular Formula: C₂₃H₂₆O₆S
• Molecular Weight: 430.522
• Mol file: 556039-05-5.mol

Synonyms:phenyl 3-O-allyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 3-O-allyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 3-O-allyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside

There total 7 articles about phenyl 3-O-allyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside 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: 94.0%

p-Anisaldehyde dimethyl acetal (2186-92-7) + phenyl 3-O-allyl-1-thio-β-D-glucopyranoside (197005-23-5) → phenyl 3-O-allyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside (556039-05-5)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1081/CAR-120019014

Reference yield: 94.0%

p-Anisaldehyde dimethyl acetal (2186-92-7) + phenyl 2,4,6-tri-O-acetyl-3-O-allyl-1-thio-β-D-glucopyranoside (197005-22-4,1820572-28-8) → phenyl 3-O-allyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside (556039-05-5)

Guidance literature:

phenyl 2,4,6-tri-O-acetyl-3-O-allyl-1-thio-β-D-glucopyranoside; With sodium methylate; In methanol;

p-Anisaldehyde dimethyl acetal;

DOI:10.1007/s007060200016

Reference yield:

thiophenol (108-98-5) → phenyl 3-O-allyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside (556039-05-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / BF₃OEt₂ / CH₂Cl₂

2: 94 percent / MeONa / methanol

With boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane;

DOI:10.1007/s007060200016

upstream raw materials:

p-Anisaldehyde dimethyl acetal

phenyl 2,4,6-tri-O-acetyl-3-O-allyl-1-thio-β-D-glucopyranoside

phenyl 3-O-allyl-1-thio-β-D-glucopyranoside

thiophenol

Downstream raw materials:

Succinic acid mono-[(2R,3R,4R,5R,6S)-4-allyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl] ester

N-Benzyl-succinamic acid (2R,3R,4R,5R,6S)-4-allyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

phenyl 3-O-allyl-4-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside