2-(trifluoroacetylamino)ethyl 2-acetylamino-4-O-(3-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(trifluoroacetylamino)ethyl 2-acetylamino-4-O-(3-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 917082-53-2
• Molecular Formula: C₄₁H₄₇F₃N₂O₁₃
• Molecular Weight: 832.825
• Mol file: 917082-53-2.mol

Synonyms:2-(trifluoroacetylamino)ethyl 2-acetylamino-4-O-(3-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property of 2-(trifluoroacetylamino)ethyl 2-acetylamino-4-O-(3-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(trifluoroacetylamino)ethyl 2-acetylamino-4-O-(3-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 8 articles about 2-(trifluoroacetylamino)ethyl 2-acetylamino-4-O-(3-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-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: 91.0%

2-(trifluoroacetylamino)ethyl 2-acetylamino-3,6-di-O-benzyl-4-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside (917082-52-1) + acetyl chloride (75-36-5) → 2-(trifluoroacetylamino)ethyl 2-acetylamino-4-O-(3-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (917082-53-2)

Guidance literature:

With pyridine; In dichloromethane; at -25 ℃; for 0.0833333h;

DOI:10.1007/s11178-006-0043-7

Reference yield:

N-[2-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-2,2,2-trifluoro-acetamide → 2-(trifluoroacetylamino)ethyl 2-acetylamino-4-O-(3-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (917082-53-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 742 mg / camphorsulfonic acid / acetonitrile / 2 h / 75 °C

2: 85 percent / sodium hydride / dimethylformamide; kerosene / -20 °C

3: 90 percent / Me₃N*BH₃; AlCl₃ / tetrahydrofuran / 30 h / 20 °C

4: 83 percent / AW-300 molecular sieves; N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / -30 - -10 °C

5: 94 percent / sodium methoxide / methanol / 1 h / 20 °C

6: 91 percent / pyridine / CH₂Cl₂ / 0.08 h / -25 °C

With pyridine; N-iodo-succinimide; aluminium trichloride; molecular sieve; trifluorormethanesulfonic acid; trimethylamine-borane; camphor-10-sulfonic acid; sodium methylate; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; kerosene;

DOI:10.1007/s11178-006-0043-7

Reference yield:

2-(trifluoroacetylamino)ethyl 2-acetylamino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (917082-48-5) → 2-(trifluoroacetylamino)ethyl 2-acetylamino-4-O-(3-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (917082-53-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / sodium hydride / dimethylformamide; kerosene / -20 °C

2: 90 percent / Me₃N*BH₃; AlCl₃ / tetrahydrofuran / 30 h / 20 °C

3: 83 percent / AW-300 molecular sieves; N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / -30 - -10 °C

4: 94 percent / sodium methoxide / methanol / 1 h / 20 °C

5: 91 percent / pyridine / CH₂Cl₂ / 0.08 h / -25 °C

With pyridine; N-iodo-succinimide; aluminium trichloride; molecular sieve; trifluorormethanesulfonic acid; trimethylamine-borane; sodium methylate; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; kerosene;

DOI:10.1007/s11178-006-0043-7

upstream raw materials:

2-(trifluoroacetylamino)ethyl 2-acetylamino-3,6-di-O-benzyl-4-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside

acetyl chloride

2-(trifluoroacetylamino)ethyl 2-acetylamino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

2-(trifluoroacetylamino)ethyl 2-acetylamino-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

Downstream raw materials:

2-(trifluoroacetylamino)ethyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->2)-(3-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-2-acetylamino-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

2-(trifluoroacetylamino)ethyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->2)-(4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-2-acetylamino-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside