methyl 2-O-(3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

Base Information

• Chemical Name: methyl 2-O-(3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside
• CAS No.: 134407-43-5
• Molecular Formula: C₃₄H₄₁N₃O₈
• Molecular Weight: 619.715
• Mol file: 134407-43-5.mol

Synonyms:methyl 2-O-(3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

Chemical Property of methyl 2-O-(3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-(3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

There total 6 articles about methyl 2-O-(3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-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: 93.0%

methyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside (134407-42-4) → methyl 2-O-(3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside (134407-43-5)

Guidance literature:

With sodium methylate; In methanol; dichloromethane; for 16h; Ambient temperature;

DOI:10.1016/0008-6215(91)84146-6

Reference yield:

(2S,3S,4S,5S,6R)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3,4-diol (20881-80-5) → methyl 2-O-(3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside (134407-43-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) dibutyltin oxide, 2.) tetrabutylammonium chloride / 1.) CH₃OH, 2 h, reflux, 2.) toluene, 1 h, reflux

2: 1.) molecular sieves (4 Angstroem), 2.) silver triflate, Br₂, Et₃N / 1.) CH₂Cl₂, 4 h, r.t., 2.) 60 min, -45 deg C

3: 93 percent / sodium methoxide / methanol; CH₂Cl₂ / 16 h / Ambient temperature

With 4 A molecular sieve; tetrabutyl-ammonium chloride; bromine; sodium methylate; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; triethylamine; In methanol; dichloromethane;

DOI:10.1016/0008-6215(91)84146-6

Reference yield:

benzyl bromide (100-39-0) → methyl 2-O-(3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside (134407-43-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) dibutyltin oxide, 2.) tetrabutylammonium chloride / 1.) CH₃OH, 2 h, reflux, 2.) toluene, 1 h, reflux

2: 1.) molecular sieves (4 Angstroem), 2.) silver triflate, Br₂, Et₃N / 1.) CH₂Cl₂, 4 h, r.t., 2.) 60 min, -45 deg C

3: 93 percent / sodium methoxide / methanol; CH₂Cl₂ / 16 h / Ambient temperature

With 4 A molecular sieve; tetrabutyl-ammonium chloride; bromine; sodium methylate; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; triethylamine; In methanol; dichloromethane;

DOI:10.1016/0008-6215(91)84146-6

upstream raw materials:

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

(2S,3S,4S,5S,6R)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3,4-diol

benzyl bromide

methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

Downstream raw materials:

methyl O-(2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-O-(3,4-di-O-benzyl-α-D-rhamnopyranosyl)-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

methyl O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-O-(3,4-di-O-benzyl-α-D-rhamnopyranosyl)-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside