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

Base Information

• Chemical Name: methyl 2,4-di-O-benzyl-6-O-(2,4-di-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside
• CAS No.: 79317-23-0
• Molecular Formula: C₄₅H₅₂O₁₃
• Molecular Weight: 800.9
• Mol file: 79317-23-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about methyl 2,4-di-O-benzyl-6-O-(2,4-di-O-acetyl-3,6-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: 50.0%

methyl 2,4-di-O-benzyl-α-D-mannopyranoside (58341-67-6,67381-34-4,86172-91-0,86342-19-0,67381-29-7) + 2,4-di-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranosyl chloride (79317-22-9) → methyl 2,4-di-O-benzyl-6-O-(2,4-di-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside (79317-23-0)

Guidance literature:

Hanessian-Banoub conditions;

DOI:10.1016/S0008-6215(00)80764-8

Reference yield:

2,4-di-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranose (79330-99-7) → methyl 2,4-di-O-benzyl-6-O-(2,4-di-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside (79317-23-0)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂, DMF / 1,2-dichloro-ethane / 14 h / 15 - 20 °C

2: 49.5 percent / AgOSO₂CF₃, 1,1,3,3-tetramethylurea / 1,2-dichloro-ethane / 21 h / 20 °C

With thionyl chloride; silver trifluoromethanesulfonate; N,N-dimethyl-formamide; tetramethylurea; In 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(83)88189-0

Reference yield:

benzyl bromide (100-39-0) → methyl 2,4-di-O-benzyl-6-O-(2,4-di-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside (79317-23-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) (Bu₃Sn)2O / 1.) toluene, reflux, 3 h; 2.) 90 deg C, 2 d

2: pyridine / 16 h / 20 °C

3: 64 percent / NaOAc, PdCl₂ / acetic acid; H₂O / 14 h / 20 °C

4: SOCl₂, DMF / 1,2-dichloro-ethane / 14 h / 15 - 20 °C

5: 49.5 percent / AgOSO₂CF₃, 1,1,3,3-tetramethylurea / 1,2-dichloro-ethane / 21 h / 20 °C

With thionyl chloride; sodium acetate; silver trifluoromethanesulfonate; N,N-dimethyl-formamide; bis(tri-n-butyltin)oxide; tetramethylurea; palladium dichloride; In pyridine; water; acetic acid; 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(83)88189-0

upstream raw materials:

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

2,4-di-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranosyl chloride

benzyl bromide

allyl α-D-mannopyranoside

Downstream raw materials:

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

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