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

Base Information

Chemical Name:ethyl 2-azido-4,6-di-O-benzyl-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside
CAS No.:1334525-93-7
Molecular Formula:C₂₂H₂₆FN₃O₃S
Molecular Weight:431.531
Hs Code.:

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

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

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

There total 12 articles about ethyl 2-azido-4,6-di-O-benzyl-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:

: C₈H₁₄FN₃O₃S

: 100-39-0
benzyl bromide

: 1334525-93-7
ethyl 2-azido-4,6-di-O-benzyl-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside

Guidance literature:: C₈H₁₄FN₃O₃S; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.333333h;

benzyl bromide; In N,N-dimethyl-formamide; at 0 - 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

: 1334525-93-7
ethyl 2-azido-4,6-di-O-benzyl-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

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

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

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

4.1: toluene-4-sulfonic acid / methanol / 20 °C

5.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C

5.2: 0 - 20 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; 15-crown-5; diethylamino-sulfur trifluoride; sodium hydride; toluene-4-sulfonic acid; sodium nitrite; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2011.05.024

Reference yield:

: 1334525-90-4
ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-trifluoromethanesulfonyl-1-thio-β-D-glucopyranoside

: 1334525-93-7
ethyl 2-azido-4,6-di-O-benzyl-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

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

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

3.1: toluene-4-sulfonic acid / methanol / 20 °C

4.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C

4.2: 0 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; 15-crown-5; diethylamino-sulfur trifluoride; sodium hydride; toluene-4-sulfonic acid; sodium nitrite; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2011.05.024