methyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1<*>2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

Base Information

• Chemical Name: methyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1<*>2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• CAS No.: 80585-62-2
• Molecular Formula: C₅₅H₆₀O₁₁
• Molecular Weight: 897.075
• Mol file: 80585-62-2.mol

Synonyms:methyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1<*>2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

Chemical Property of methyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1<*>2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1<*>2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

There total 12 articles about methyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1<*>2)-3,4,6-tri-O-benzyl-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: 99.0%

methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1<*>2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside (80596-05-0) → methyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1<*>2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside (80585-62-2)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1055/s-0032-1316685

Reference yield:

methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside (20672-67-7) → methyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1<*>2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside (80585-62-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 77.8 percent / N-iodosuccinimide, 4A molecular sieves, trifluoromethanesulfonic acid / CH₂Cl₂ / 0.5 h / -10 °C

2: 94 percent / NaOMe / methanol / Ambient temperature

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sodium methylate; In methanol; dichloromethane;

DOI:10.1016/0008-6215(95)00073-3

Reference yield:

3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose (16697-49-7) → methyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1<*>2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside (80585-62-2)

Guidance literature:

Multi-step reaction with 3 steps

1: HBr / diethyl ether / Ambient temperature

2: 1) molecular sieves 4 Angstroem, Ag-triflate / 1) CH₂Cl₂, -78 deg C, 0.5h, 2a) -78 deg C, 1h, 2b) -78 deg C to RT, 12h

3: NaOMe / methanol / Ambient temperature

With 4 A molecular sieve; hydrogen bromide; sodium methylate; silver trifluoromethanesulfonate; In methanol; diethyl ether;

upstream raw materials:

methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1<*>2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside

ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside

Downstream raw materials:

methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-6D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside