2-O-acetyl-3,6-di-O-benzyl-4-O-levulinate-α-D-mannopyranoside trichloroacetimidate

Base Information

• Chemical Name: 2-O-acetyl-3,6-di-O-benzyl-4-O-levulinate-α-D-mannopyranoside trichloroacetimidate
• CAS No.: 383367-62-2
• Molecular Formula: C₂₉H₃₂Cl₃NO₉
• Molecular Weight: 644.933
• Mol file: 383367-62-2.mol

Synonyms:2-O-acetyl-3,6-di-O-benzyl-4-O-levulinate-α-D-mannopyranoside trichloroacetimidate

Chemical Property of 2-O-acetyl-3,6-di-O-benzyl-4-O-levulinate-α-D-mannopyranoside trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-acetyl-3,6-di-O-benzyl-4-O-levulinate-α-D-mannopyranoside trichloroacetimidate

There total 1 articles about 2-O-acetyl-3,6-di-O-benzyl-4-O-levulinate-α-D-mannopyranoside trichloroacetimidate 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: 98.0%

4-Oxo-pentanoic acid (2R,3R,4S,5S)-5-acetoxy-4-benzyloxy-2-benzyloxymethyl-6-hydroxy-tetrahydro-pyran-3-yl ester + trichloroacetonitrile (545-06-2) → 2-O-acetyl-3,6-di-O-benzyl-4-O-levulinate-α-D-mannopyranoside trichloroacetimidate (383367-62-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -20 - 20 ℃; for 2h;

DOI:10.1021/ol016631v

Reference yield: 74.0%

n-Pent-4-enyl alcohol (821-09-0) + 2-O-acetyl-3,6-di-O-benzyl-4-O-levulinate-α-D-mannopyranoside trichloroacetimidate (383367-62-2) → n-pentenyl 2-O-acetyl-3,6-di-O-benzyl-4-O-levulinate-α-D-mannopyranoside (383367-65-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1002/hlca.200390331

Reference yield:

2-O-acetyl-3,6-di-O-benzyl-4-O-levulinate-α-D-mannopyranoside trichloroacetimidate (383367-62-2) → n-pentenyl-2-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranoside (383367-66-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / TMSOTf / CH₂Cl₂

2: 71 percent / NH₂NH₂ / acetic acid; pyridine

With trimethylsilyl trifluoromethanesulfonate; hydrazine; In pyridine; dichloromethane; acetic acid;

DOI:10.1002/hlca.200390331

upstream raw materials:

trichloroacetonitrile

Downstream raw materials:

n-pentenyl 2-O-acetyl-3,6-di-O-benzyl-4-O-levulinate-α-D-mannopyranoside

n-4-pentenyl 3,4,6-tri-O-benzyl-2-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-α-D-mannopyranoside

n-pentenyl-2-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranoside