ethyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: ethyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside
• CAS No.: 134407-35-5
• Molecular Formula: C₃₇H₄₅N₃O₈S
• Molecular Weight: 691.846
• Mol file: 134407-35-5.mol

Synonyms:

Chemical Property of ethyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside

There total 1 articles about ethyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-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:

1,2-di-O-acetyl-3,4-di-O-benzyl-6-deoxy-α-D-mannopyranose (134524-12-2) → ethyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside (134407-35-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / boron trifluoride etherate, molecular sieves (4 Angstroem) / CH₂Cl₂ / 8 h / Ambient temperature

2: 1.) Br₂, cyclohexene, 2.) mercuric cyanide, mercuric bromide, molecular sieves (4 Angstroem) / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, a) 0 deg C, 4 h, b.) 16 h

With 4 A molecular sieve; boron trifluoride diethyl etherate; bromine; mercury(II) cyanide; mercury dibromide; cyclohexene; In dichloromethane;

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

Reference yield:

ethyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside (134407-35-5) → methyl O-(3,4-di-O-benzyl-α-D-rhamnopyranosyl)-(1->2)-O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-3,4-di-O-benzyl-α-D-rhamnopyranoside (136737-18-3)

Guidance literature:

Multi-step reaction with 2 steps

2: 59 percent / NaOMe / CH₂Cl₂; methanol / 16 h / Ambient temperature

With sodium methylate; In methanol; dichloromethane;

DOI:10.1016/0008-6215(92)84151-H

Reference yield:

ethyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-D-rhamnopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside (134407-35-5) → methyl O-(3,4-di-O-benzyl-α-D-rhamnopyranosyl)-(1->2)-O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside (134407-40-2)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 92 percent / sodium methoxide / methanol; CH₂Cl₂ / 16 h / Ambient temperature

With 4 A molecular sieve; bromine; sodium methylate; silver trifluoromethanesulfonate; triethylamine; In methanol; dichloromethane;

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

upstream raw materials:

1,2-di-O-acetyl-3,4-di-O-benzyl-6-deoxy-α-D-mannopyranose

Downstream raw materials:

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

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

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