methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-β-D-xylo-hexopyranoside

Base Information

• Chemical Name: methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-β-D-xylo-hexopyranoside
• CAS No.: 108740-01-8
• Molecular Formula: C₂₁H₂₄O₅
• Molecular Weight: 356.419
• Mol file: 108740-01-8.mol

Synonyms:methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-β-D-xylo-hexopyranoside

Chemical Property of methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-β-D-xylo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-β-D-xylo-hexopyranoside

There total 15 articles about methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-β-D-xylo-hexopyranoside 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: 98.0%

benzyl bromide (100-39-0) + methyl 4,6-O-benzylidene-3-deoxy-β-D-xylo-hexopyranoside (108740-00-7) → methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-β-D-xylo-hexopyranoside (108740-01-8)

Guidance literature:

With sodium methylsulfinylmethanide; for 3.5h;

DOI:10.1016/S0008-6215(00)90292-1

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-β-D-xylo-hexopyranoside (108740-01-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / toluene-p-sulfonic acid / acetonitrile / 16 h / Ambient temperature

3: 96 percent / pyridine

4: 79 percent / tributyltin hydride / toluene / Heating

5: 98 percent / 0.1M sodium methoxide / CH₂Cl₂; methanol / 16 h

6: 98 percent / sodium methylsulfinylmethanide / 3.5 h

With pyridine; tri-n-butyl-tin hydride; sodium methylate; sodium methylsulfinylmethanide; toluene-4-sulfonic acid; In methanol; dichloromethane; toluene; acetonitrile;

DOI:10.1016/S0008-6215(00)90292-1

Reference yield:

methyl 2-O-acetyl-4,6-O-benzylidene-3-deoxy-β-D-xylo-hexopyranoside (108739-99-7) → methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-β-D-xylo-hexopyranoside (108740-01-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / 0.1M sodium methoxide / CH₂Cl₂; methanol / 16 h

2: 98 percent / sodium methylsulfinylmethanide / 3.5 h

With sodium methylate; sodium methylsulfinylmethanide; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(00)90292-1

upstream raw materials:

benzyl bromide

methyl 2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

methyl 3,4-di-O-benzyl-α-D-mannopyranoside

Downstream raw materials:

methyl 2,6-di-O-benzyl-3-deoxy-β-D-xylo-hexopyranoside