Benzyl 2-Acetamido-3,4-di-O-acetyl-2-deoxy-6-O-(tri-O-benzyl-L-fucopyranosyl)- α-D-glucopyranoside (4:1 α/β mixture)

Base Information

• Chemical Name: Benzyl 2-Acetamido-3,4-di-O-acetyl-2-deoxy-6-O-(tri-O-benzyl-L-fucopyranosyl)- α-D-glucopyranoside (4:1 α/β mixture)
• CAS No.: 33639-78-0
• Molecular Formula: C₄₆H₅₃NO₁₂
• Molecular Weight: 811.926
• Mol file: 33639-78-0.mol

Synonyms:Benzyl 2-Acetamido-3,4-di-O-acetyl-2-deoxy-6-O-(tri-O-benzyl-L-fucopyranosyl)- α-D-glucopyranoside (4:1 α/β mixture)

Chemical Property of Benzyl 2-Acetamido-3,4-di-O-acetyl-2-deoxy-6-O-(tri-O-benzyl-L-fucopyranosyl)- α-D-glucopyranoside (4:1 α/β mixture)

Chemical Property:

• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

Benzyl2-Acetamido-3,4-di-O-acetyl-2-deoxy-6-O-(tri-O-benzyl-L-fucopyranosyl)-α-D-glucopyranoside(4:1α/βmixture) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl 2-Acetamido-3,4-di-O-acetyl-2-deoxy-6-O-(tri-O-benzyl-L-fucopyranosyl)- α-D-glucopyranoside (4:1 α/β mixture)

There total 3 articles about Benzyl 2-Acetamido-3,4-di-O-acetyl-2-deoxy-6-O-(tri-O-benzyl-L-fucopyranosyl)- α-D-glucopyranoside (4:1 α/β mixture) 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: 57.2%

benzyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-glucopyranoside (33401-01-3,55652-76-1) + tribenzyl-α-L-rhamnopyranosyl bromide → benzyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-(2,3,4-tri-O-benzyl-β-L-rhamnopyranosyl)-α-D-glucopyranoside (110901-00-3,33639-78-0)

Guidance literature:

With silver silicate; In dichloromethane; at 0 ℃; for 2h;

Reference yield: 54.0%

benzyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-glucopyranoside (33401-01-3,55652-76-1) + ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (116514-50-2,128962-63-0,131545-02-3,136758-06-0,99409-34-4,116391-11-8) → benzyl 2-acetamido-3,4-di-O-acetyl-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-α-D-glucopyranoside (33639-78-0)

Guidance literature:

ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside; With tetrabutylammomium bromide; copper(ll) bromide; In dichloromethane; N,N-dimethyl-formamide; at 21 ℃; for 4h; Molecular sieve;

benzyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-glucopyranoside; In dichloromethane; N,N-dimethyl-formamide; at 21 ℃; for 64h; Molecular sieve;

DOI:10.1007/s11172-015-0990-7

Reference yield:

1-O-Acetyl-2,3,4-tri-O-benzyl-β-L-rhamnopyranose (110809-95-5) → benzyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-(2,3,4-tri-O-benzyl-β-L-rhamnopyranosyl)-α-D-glucopyranoside (110901-00-3,33639-78-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / Me₃SiBr / CH₂Cl₂ / 2 h / Ambient temperature

2: 57.2 percent / silver silicate / CH₂Cl₂ / 2 h / 0 °C

With trimethylsilyl bromide; silver silicate; In dichloromethane;

upstream raw materials:

benzyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-glucopyranoside

1-O-Acetyl-2,3,4-tri-O-benzyl-β-L-rhamnopyranose

ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

Refernces

• 1、 Kamiya, Shintaro,Esaki, Sachiko,Shiba, Naoko. "Syntheses of Certain 2-Acetamido-2-deoxy-O-(L-rhamnopyranosyl)-D-glucopyranoses". . p. 1195 - 1198. Retrieved 2007/10/02.