ethyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside

Base Information

• Chemical Name: ethyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside
• CAS No.: 134407-32-2
• Molecular Formula: C₂₄H₃₀O₅S
• Molecular Weight: 430.565
• Mol file: 134407-32-2.mol

Synonyms:ethyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside

Chemical Property of ethyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside

There total 1 articles about ethyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside 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: 64.0%

1,2-di-O-acetyl-3,4-di-O-benzyl-6-deoxy-α-D-mannopyranose (134524-12-2) + ethanethiol (75-08-1) → ethyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-β-D-rhamnopyranoside (134407-34-4) + ethyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside (134407-32-2)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; for 8h; Ambient temperature;

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

Reference yield: 97.0%

ethyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside (134407-32-2) → ethyl 3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside (134407-33-3)

Guidance literature:

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

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

Reference yield:

ethyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside (134407-32-2) → 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 2 steps

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

2: 93 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

ethanethiol

Downstream 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

ethyl 3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside

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