ethyl 2-trifluoroacetamido-3,4,6-tri-O-benzoyl-1-thio-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 2-trifluoroacetamido-3,4,6-tri-O-benzoyl-1-thio-2-deoxy-β-D-glucopyranoside
• CAS No.: 1429306-54-6
• Molecular Formula: C₃₁H₂₈F₃NO₈S
• Molecular Weight: 631.626
• Mol file: 1429306-54-6.mol

Synonyms:ethyl 2-trifluoroacetamido-3,4,6-tri-O-benzoyl-1-thio-2-deoxy-β-D-glucopyranoside

Chemical Property of ethyl 2-trifluoroacetamido-3,4,6-tri-O-benzoyl-1-thio-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-trifluoroacetamido-3,4,6-tri-O-benzoyl-1-thio-2-deoxy-β-D-glucopyranoside

There total 2 articles about ethyl 2-trifluoroacetamido-3,4,6-tri-O-benzoyl-1-thio-2-deoxy-β-D-glucopyranoside 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: 92.0%

ethyl 2-trifluoroacetamido-1-thio-2-deoxy-β-D-glucopyranoside (1429306-52-4) + benzoyl chloride (98-88-4) → ethyl 2-trifluoroacetamido-3,4,6-tri-O-benzoyl-1-thio-2-deoxy-β-D-glucopyranoside (1429306-54-6)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1016/j.carres.2013.01.008

Reference yield:

ethyl 2-trifluoroacetamido-3,4,6-tri-O-acetyl-1-thio-2-deoxy-β-D-glucopyranoside → ethyl 2-trifluoroacetamido-3,4,6-tri-O-benzoyl-1-thio-2-deoxy-β-D-glucopyranoside (1429306-54-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium; methanol / 2 h / 20 °C

1.2: Amberlyst resin [IR₁₂₀ (H⁺)]

2.1: dmap; pyridine / dichloromethane / 48 h / 20 °C / Inert atmosphere

With pyridine; methanol; dmap; sodium; In dichloromethane;

DOI:10.1016/j.carres.2013.01.008

Reference yield: 95.0%

ethyl 2-trifluoroacetamido-3,4,6-tri-O-benzoyl-1-thio-2-deoxy-β-D-glucopyranoside (1429306-54-6) + 6-O-(2-trifluoroacetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl)-2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl azide (1429306-58-0) → 6-O-[6-O-(2-trifluoroacetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl)-2-trifluoroacetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl]-2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl azide (1429306-59-1)

Guidance literature:

ethyl 2-trifluoroacetamido-3,4,6-tri-O-benzoyl-1-thio-2-deoxy-β-D-glucopyranoside; 6-O-(2-trifluoroacetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl)-2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl azide; With N-iodo-succinimide; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 19h; Inert atmosphere;

DOI:10.1016/j.carres.2013.01.008

upstream raw materials:

ethyl 2-trifluoroacetamido-1-thio-2-deoxy-β-D-glucopyranoside

benzoyl chloride

Downstream raw materials:

6-O-(2-trifluoroacetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl)-2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl azide

6-O-[6-O-(2-trifluoroacetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl)-2-trifluoroacetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl]-2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl azide

6-O-[6-O-(6-O-[2-trifluoroacetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl]-2-trifluoroacetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl)-2-trifluoroacetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl]-2-acetamido-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl azide