ethyl 2-azido-4,6-O-benzylidene-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 2-azido-4,6-O-benzylidene-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside
• CAS No.: 1334525-92-6
• Molecular Formula: C₁₅H₁₈FN₃O₃S
• Molecular Weight: 339.391
• Mol file: 1334525-92-6.mol

Synonyms:ethyl 2-azido-4,6-O-benzylidene-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 2-azido-4,6-O-benzylidene-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-azido-4,6-O-benzylidene-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside

There total 10 articles about ethyl 2-azido-4,6-O-benzylidene-2,3-dideoxy-3-fluoro-1-thio-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: 55.0%

ethyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-allopyranoside (1334525-91-5) → ethyl 2-azido-4,6-O-benzylidene-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside (1334525-92-6)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; at -40 - 20 ℃;

DOI:10.1016/j.carres.2011.05.024

Reference yield:

ethyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside → ethyl 2-azido-4,6-O-benzylidene-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside (1334525-92-6)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / dichloromethane / 20 °C / Inert atmosphere; Cooling with ice

2: N,N,N,N,N,N-hexamethylphosphoric triamide; 15-crown-5; sodium nitrite / 12 h / 20 °C / Inert atmosphere

3: diethylamino-sulfur trifluoride / dichloromethane / -40 - 20 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; 15-crown-5; diethylamino-sulfur trifluoride; sodium nitrite; In dichloromethane;

DOI:10.1016/j.carres.2011.05.024

Reference yield:

ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-trifluoromethanesulfonyl-1-thio-β-D-glucopyranoside (1334525-90-4) → ethyl 2-azido-4,6-O-benzylidene-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside (1334525-92-6)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N,N,N,N,N-hexamethylphosphoric triamide; 15-crown-5; sodium nitrite / 12 h / 20 °C / Inert atmosphere

2: diethylamino-sulfur trifluoride / dichloromethane / -40 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; 15-crown-5; diethylamino-sulfur trifluoride; sodium nitrite; In dichloromethane;

DOI:10.1016/j.carres.2011.05.024

upstream raw materials:

ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-trifluoromethanesulfonyl-1-thio-β-D-glucopyranoside

ethyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-allopyranoside

2-deoxy-2-amino glucose

2-deoxy-2-phthalimido-D-glucopyranose

Downstream raw materials:

ethyl 2-azido-4,6-di-O-benzyl-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside

Refernces