methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside
• CAS No.: 99212-41-6
• Molecular Formula: C₂₃H₂₆O₇
• Molecular Weight: 414.455
• Mol file: 99212-41-6.mol

Synonyms:methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

Chemical Property of methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

There total 6 articles about methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-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: 95.0%

acetic anhydride (108-24-7) + methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (76375-66-1) → methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (99212-41-6)

Guidance literature:

With pyridine; dmap; at 20 ℃;

DOI:10.1080/07328300802030787

Reference yield: 92.0%

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (76375-66-1) + acetyl chloride (75-36-5) → methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (99212-41-6)

Guidance literature:

With pyridine; dmap; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1039/a707346a

Reference yield:

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (99212-41-6)

Guidance literature:

Multi-step reaction with 2 steps

1: (nBu₃Sn)2O / toluene

2: pyridine

With pyridine; bis(tri-n-butyltin)oxide; In toluene; 1: Cyclization / 1: Ring cleavage / 2: Acetylation;

DOI:10.1002/1521-3773(20000616)39:12<2160::AID-ANIE2160>3.0.CO;2-E

upstream raw materials:

methyl 4,6-O-benzylidene-α-D-galactopyranoside

acetic anhydride

benzyl bromide

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

Downstream raw materials:

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside

methyl 3-O-acetyl-2-O-benzyl-α-D-glucopyranoside

methyl 2,6-di-O-benzyl-3-O-acetyl-α-D-glucopyranoside

(2S,3S,6R)-3-Benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-one