2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranosyl)-D-glucopyranose

Base Information

Chemical Name:2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranosyl)-D-glucopyranose
CAS No.:121865-27-8
Molecular Formula:C₄₃H₄₉N₃O₁₀
Molecular Weight:767.876
Hs Code.:

Synonyms:2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranosyl)-D-glucopyranose

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Chemical Property of 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranosyl)-D-glucopyranose

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Technology Process of 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranosyl)-D-glucopyranose

There total 6 articles about 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranosyl)-D-glucopyranose 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: 82.0%

: 121845-05-4
tert-butyldimethylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside

: 121865-27-8
2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranosyl)-D-glucopyranose

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; at -15 ℃; for 3h;

Reference yield:

: 121865-28-9
tert-butyldimethylsilyl 2-azido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside

: 121865-27-8
2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranosyl)-D-glucopyranose

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) dibutyltin oxide, 2.) tetrabutylammonium iodide / 1.) MeOH, reflux, 15 h, 2.) toluene, 60 degC, 24 h

2: 61 percent / p-toluenesulfonic acid monohydrate / 24 h / Ambient temperature

3: 79 percent / NaH / dimethylformamide / 6 h / -10 °C

4: 82 percent / 1 M tetrabutylammonium fluoride / CH₂Cl₂; tetrahydrofuran / 3 h / -15 °C

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

: 96255-92-4
tert-Butyldimethylsilyl-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-azido-2-desoxy-β-D-glucopyranosid

: 121865-27-8
2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranosyl)-D-glucopyranose

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / NaOMe / methanol / 3 h / Ambient temperature

2: 1.) dibutyltin oxide, 2.) tetrabutylammonium iodide / 1.) MeOH, reflux, 15 h, 2.) toluene, 60 degC, 24 h

3: 61 percent / p-toluenesulfonic acid monohydrate / 24 h / Ambient temperature

4: 79 percent / NaH / dimethylformamide / 6 h / -10 °C

5: 82 percent / 1 M tetrabutylammonium fluoride / CH₂Cl₂; tetrahydrofuran / 3 h / -15 °C

With tetrabutyl ammonium fluoride; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;