methyl 2,4-di-O-benzyl-3-O-(2,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside

Base Information

• Chemical Name: methyl 2,4-di-O-benzyl-3-O-(2,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside
• CAS No.: 79218-61-4
• Molecular Formula: C₄₁H₄₈O₁₁
• Molecular Weight: 716.826
• Mol file: 79218-61-4.mol

Synonyms:methyl 2,4-di-O-benzyl-3-O-(2,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside

Chemical Property of methyl 2,4-di-O-benzyl-3-O-(2,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl 2,4-di-O-benzyl-3-O-(2,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside

There total 4 articles about methyl 2,4-di-O-benzyl-3-O-(2,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside 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: 79.1%

methyl 6-O-benzoyl-2,4-di-O-benzyl-3-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside (79218-62-5) → methyl 2,4-di-O-benzyl-3-O-(2,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside (79218-61-4)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 16h;

DOI:10.1016/S0008-6215(00)80752-1

Reference yield: 48.8%

Acetic acid (2R,3R,4S,5S,6R)-2-acetoxymethyl-3,5-bis-benzyloxy-6-((2R,3R,4S,5S,6S)-3,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-4-yl ester (79218-63-6) → methyl 2,4-di-O-benzyl-3-O-(2,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside (79218-61-4)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 16h;

DOI:10.1016/S0040-4020(01)92346-4

Reference yield:

methyl 2,4-di-O-benzyl-α-D-mannopyranoside (58341-67-6,67381-34-4,86172-91-0,86342-19-0,67381-29-7) → methyl 2,4-di-O-benzyl-3-O-(2,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside (79218-61-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 87.5 percent / pyridine / 32 h / 20 °C

2: 67.7 percent / AgSO₃CF₃, Me₂NCONMe₂ / CH₂Cl₂ / 22 h / 20 °C / 6 added in two portions. Two-thirds: -10 to -15 deg C, 20 deg C, 6 h; the rest: -10 to -15 deg C, 20 deg C, 16 h

3: 79.1 percent / NaOMe / methanol / 16 h / 20 °C

With pyridine; sodium methylate; silver trifluoromethanesulfonate; tetramethylurea; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(00)80752-1

upstream raw materials:

methyl 6-O-benzoyl-2,4-di-O-benzyl-3-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside

Acetic acid (2R,3R,4S,5S,6R)-2-acetoxymethyl-3,5-bis-benzyloxy-6-((2R,3R,4S,5S,6S)-3,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-4-yl ester

methyl 2,4-di-O-benzyl-α-D-mannopyranoside

methyl 6-O-benzoyl-2,4-di-O-benzyl-α-D-mannopyranoside

Downstream raw materials:

methyl 6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-3-O-<3,6-di-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranosyl>-α-D-mannopyranoside