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

Base Information

• Chemical Name: methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-α-D-galactopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-β-D-glucopyranoside
• CAS No.: 1313374-94-5
• Molecular Formula: C₄₆H₄₆O₁₅
• Molecular Weight: 838.862
• Mol file: 1313374-94-5.mol

Synonyms:methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-α-D-galactopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-β-D-glucopyranoside

Chemical Property of methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-α-D-galactopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-α-D-galactopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-β-D-glucopyranoside

There total 9 articles about methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-α-D-galactopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-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: 70.8%

methyl 3,4,6-tri-O-benzoyl-β-D-glucopyranoside (51996-09-9) + isopropyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (1313374-84-3) → methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-β-D-glucopyranoside (1313374-95-6) + methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-α-D-galactopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-β-D-glucopyranoside (1313374-94-5)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 2h; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.carres.2011.03.012

Reference yield:

benzoyl chloride (98-88-4) → methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-β-D-glucopyranoside (1313374-95-6) + methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-α-D-galactopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-β-D-glucopyranoside (1313374-94-5)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / dichloromethane / 20 °C / Cooling with ice

2: acetyl chloride / methanol / 20 °C

3: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -20 °C / Inert atmosphere

With pyridine; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; acetyl chloride; In methanol; dichloromethane;

DOI:10.1016/j.carres.2011.03.012

Reference yield:

isopropyl 3-O-allyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (1313374-85-4) → methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-β-D-glucopyranoside (1313374-95-6) + methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-α-D-galactopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-β-D-glucopyranoside (1313374-94-5)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 20 °C

2: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -20 °C / Inert atmosphere

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In pyridine; dichloromethane;

DOI:10.1016/j.carres.2011.03.012

upstream raw materials:

isopropyl 3-O-allyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

methyl 2-O-acetyl-3-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside

methyl 2-O-acetyl-3-O-benzoyl-β-D-glucopyranoside

methyl 3,4,6-tri-O-benzoyl-β-D-glucopyranoside