p-methoxybenzyl 5-azido-5,6-dideoxy-6-fluoro-2,3-O-isopropylidene-β-L-gulofuranoside

Base Information

• Chemical Name: p-methoxybenzyl 5-azido-5,6-dideoxy-6-fluoro-2,3-O-isopropylidene-β-L-gulofuranoside
• CAS No.: 1448356-29-3
• Molecular Formula: C₁₇H₂₂FN₃O₅
• Molecular Weight: 367.377
• Mol file: 1448356-29-3.mol

Synonyms:p-methoxybenzyl 5-azido-5,6-dideoxy-6-fluoro-2,3-O-isopropylidene-β-L-gulofuranoside

Chemical Property of p-methoxybenzyl 5-azido-5,6-dideoxy-6-fluoro-2,3-O-isopropylidene-β-L-gulofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-methoxybenzyl 5-azido-5,6-dideoxy-6-fluoro-2,3-O-isopropylidene-β-L-gulofuranoside

There total 3 articles about p-methoxybenzyl 5-azido-5,6-dideoxy-6-fluoro-2,3-O-isopropylidene-β-L-gulofuranoside 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: 86.0%

C18H22F4O8S → p-methoxybenzyl 5-azido-5,6-dideoxy-6-fluoro-2,3-O-isopropylidene-β-L-gulofuranoside (1448356-29-3)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 40 ℃; for 15h;

DOI:10.1021/jo401041s

Reference yield:

p-methoxybenzyl 6-deoxy-6-fluoro-2,3-O-isopropylidene-α-D-mannofuranoside (1448356-28-2) → p-methoxybenzyl 5-azido-5,6-dideoxy-6-fluoro-2,3-O-isopropylidene-β-L-gulofuranoside (1448356-29-3)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / dichloromethane / 1 h / -20 °C / Inert atmosphere

2: sodium azide / N,N-dimethyl-formamide / 15 h / 40 °C

With pyridine; sodium azide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo401041s

Reference yield:

4-methoxybenzyl 5,6-anhydro-2,3-O-isopropylidene-α-D-mannofuranoside (201678-24-2) → p-methoxybenzyl 5-azido-5,6-dideoxy-6-fluoro-2,3-O-isopropylidene-β-L-gulofuranoside (1448356-29-3)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrabutylammonium bifluoride / 60 h / 95 °C / Inert atmosphere

2: pyridine / dichloromethane / 1 h / -20 °C / Inert atmosphere

3: sodium azide / N,N-dimethyl-formamide / 15 h / 40 °C

With pyridine; sodium azide; tetrabutylammonium bifluoride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo401041s

upstream raw materials:

p-methoxybenzyl 6-deoxy-6-fluoro-2,3-O-isopropylidene-α-D-mannofuranoside

4-methoxybenzyl 5,6-anhydro-2,3-O-isopropylidene-α-D-mannofuranoside