benzyl 4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-azido-2-deoxy-β-D-glucopyranoside

Base Information

Chemical Name:benzyl 4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-azido-2-deoxy-β-D-glucopyranoside
CAS No.:138133-82-1
Molecular Formula:C₃₁H₃₉N₃O₁₆
Molecular Weight:709.661
Hs Code.:

Synonyms:benzyl 4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-azido-2-deoxy-β-D-glucopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of benzyl 4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-azido-2-deoxy-β-D-glucopyranoside

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Technology Process of benzyl 4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-azido-2-deoxy-β-D-glucopyranoside

There total 5 articles about benzyl 4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-azido-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: 54.0%

: 138133-81-0
Acetic acid (2R,3S,4R,5R,6R)-2-acetoxymethyl-5-azido-6-bromo-4-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

: 100-51-6,185532-71-2
benzyl alcohol

: 138133-82-1
benzyl 4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-azido-2-deoxy-β-D-glucopyranoside

Guidance literature:: With calcium sulfate; silver carbonate; In nitromethane; at -15 ℃; for 20h;
DOI:10.1016/0008-6215(91)89048-K

Reference yield:

: Acetic acid (2R,3S,4R,5R)-6-acetoxy-2-acetoxymethyl-5-azido-4-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

: 138133-82-1
benzyl 4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-azido-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 85 percent / HBr / aq. acetic acid / 4 h / Ambient temperature

2: 54 percent / Drierite, Ag₂CO₃ / nitromethane / 20 h / -15 °C

With calcium sulfate; hydrogen bromide; silver carbonate; In nitromethane; acetic acid;
DOI:10.1016/0008-6215(91)89048-K

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 108-24-7
acetic anhydride

: 138133-83-2
(2R,3R,4S,5S,6R)-2-((2R,3R,4R,5S,6R)-3-Azido-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

: benzyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

: 138133-82-1
benzyl 4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-azido-2-deoxy-β-D-glucopyranoside

: benzyl 3-O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

: 138133-84-3
benzyl 4,6-di-O-acetyl-3-O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-2-azido-2-deoxy-β-D-glucopyranoside

Guidance literature:: With pyridine; toluene-4-sulfonic acid; Yield given. Multistep reaction. Yields of byproduct given; 1.) DMF, 40-50 deg C, 6,5 h, 2.) r.t., overnight;
DOI:10.1016/0008-6215(91)89048-K