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

Base Information

Chemical Name: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
CAS No.:138133-84-3
Molecular Formula:C₃₄H₃₉N₃O₁₄
Molecular Weight:713.695
Hs Code.:

Synonyms: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

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

There total 1 articles about 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 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:

: 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

Reference yield: 85.0%

: 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

: 138133-90-1
benzyl 4,6-di-O-acetyl-3-O-(2,3-di-O-acetyl-β-D-glucopyranosyl)-2-azido-2-deoxy-β-D-glucopyranoside

Guidance literature:: With acetic acid; at 70 - 80 ℃; for 1.5h;
DOI:10.1016/0008-6215(91)89048-K

Reference yield:

: 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

: 138133-94-5
benzyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / 80percent aq. acetic acid / 1.5 h / 70 - 80 °C

2: 1,) pyridine, 4-dimethylaminopyridine (DMAP) / 1.) 50 deg C, 20 h, 2.) r.t., 2 h

3: 1.) CrO₃, 3.5 M sulfuric acid / 1.) acetone, r.t., 4.5 h, 2.) ethyl acetate, ether

4: NiCl₂*6H₂O, boric acid, NaBH₄ / 1.) ethanol, ethyl acetate, 1 h, 2.) r.t., 2 h

With pyridine; chromium(VI) oxide; dmap; sodium tetrahydroborate; sulfuric acid; boric acid; acetic acid; nickel dichloride;
DOI:10.1016/0008-6215(91)89048-K