2-[2-(2-Azidoethoxy)ethoxy]ethyl 3,4,6-tri-O-acetyl-2-N-acetamido-2-deoxy-β-D-glucopyranoside

Base Information

Chemical Name:2-[2-(2-Azidoethoxy)ethoxy]ethyl 3,4,6-tri-O-acetyl-2-N-acetamido-2-deoxy-β-D-glucopyranoside
CAS No.:86520-53-8
Molecular Formula:C₂₀H₃₂N₄O₁₁
Molecular Weight:504.494
Hs Code.:

Synonyms:2-[2-(2-Azidoethoxy)ethoxy]ethyl 3,4,6-tri-O-acetyl-2-N-acetamido-2-deoxy-β-D-glucopyranoside

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Chemical Property of 2-[2-(2-Azidoethoxy)ethoxy]ethyl 3,4,6-tri-O-acetyl-2-N-acetamido-2-deoxy-β-D-glucopyranoside

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Technology Process of 2-[2-(2-Azidoethoxy)ethoxy]ethyl 3,4,6-tri-O-acetyl-2-N-acetamido-2-deoxy-β-D-glucopyranoside

There total 2 articles about 2-[2-(2-Azidoethoxy)ethoxy]ethyl 3,4,6-tri-O-acetyl-2-N-acetamido-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: 90.0%

: 86520-52-7
2-[2-(2-azidoethoxy)ethoxy]ethanol

: 3068-34-6
Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

: 86520-53-8
2-[2-(2-Azidoethoxy)ethoxy]ethyl 3,4,6-tri-O-acetyl-2-N-acetamido-2-deoxy-β-D-glucopyranoside

Guidance literature:: With silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane; for 20h; Ambient temperature;
DOI:10.1016/0008-6215(86)80016-7

Reference yield: 90.0%

: 3068-34-6,38874-23-6,41355-44-6,51236-40-9,74081-14-4,79897-03-3,100759-09-9,109581-83-1
2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride

: 86520-52-7
2-[2-(2-azidoethoxy)ethoxy]ethanol

: 86520-53-8
2-[2-(2-Azidoethoxy)ethoxy]ethyl 3,4,6-tri-O-acetyl-2-N-acetamido-2-deoxy-β-D-glucopyranoside

Guidance literature:: With silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane; at 20 ℃; for 20h;
DOI:10.1002/cplu.201200014

Reference yield:

: 86520-53-8
2-[2-(2-Azidoethoxy)ethoxy]ethyl 3,4,6-tri-O-acetyl-2-N-acetamido-2-deoxy-β-D-glucopyranoside

: (S)-2-{2-[(S)-3-(2-{2-[2-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethoxy]-ethoxy}-ethylcarbamoyl)-2-amino-propionylamino]-acetylamino}-3-benzyloxy-propionic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: MeONa; MeOH / 3 h / 20 °C

2: H₂ / Pd/C / methanol / 3 h / 20 °C

3: 77 percent / EEDQ / ethanol; benzene / 24 h / 20 °C

4: piperidine / dimethylformamide / 2 h / 20 °C

With piperidine; methanol; hydrogen; sodium methylate; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; palladium on activated charcoal; In methanol; ethanol; N,N-dimethyl-formamide; benzene; 1: Deacetylation / 2: Catalytic hydrogenation / 3: Acylation / 4: Deacylation;
DOI:10.1039/b001612h