3-O-(4-azido-3-chlorobenzyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Base Information

Chemical Name:3-O-(4-azido-3-chlorobenzyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
CAS No.:617698-90-5
Molecular Formula:C₁₉H₂₄ClN₃O₆
Molecular Weight:425.869
Hs Code.:

Synonyms:3-O-(4-azido-3-chlorobenzyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

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Chemical Property of 3-O-(4-azido-3-chlorobenzyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

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Technology Process of 3-O-(4-azido-3-chlorobenzyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

There total 1 articles about 3-O-(4-azido-3-chlorobenzyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 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: 98.0%

: 193887-70-6
4-azido-3-chlorobenzyl bromide

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 617698-90-5
3-O-(4-azido-3-chlorobenzyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Guidance literature:: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.25h;

4-azido-3-chlorobenzyl bromide; In N,N-dimethyl-formamide; for 3h; Further stages.;
DOI:10.1002/ejoc.200300248

Reference yield: 61.0%

: 98-88-4
benzoyl chloride

: 617698-90-5
3-O-(4-azido-3-chlorobenzyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 3-O-(4-azido-3-chlorobenzyl)-2,4,6-tri-O-benzoyl-α/β-D-glucopyranosyl benzoate

Guidance literature:: 3-O-(4-azido-3-chlorobenzyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; With hydrogenchloride; In 1,4-dioxane; at 20 ℃;

benzoyl chloride; In pyridine; for 3h; Further stages.;
DOI:10.1002/ejoc.200300248

Reference yield:

: 617698-90-5
3-O-(4-azido-3-chlorobenzyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 4-(hydroxymethyl)benzyl 3-O-(4-azido-3-chlorobenzyl)-4,6-di-O-benzyl-β-D-glucopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->6)]-4,6-di-O-benzyl-β-D-glucopyranosyl-(1->3)-4,6-di-O-benzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: hydrogen chloride / dioxane / 20 °C

1.2: 61 percent / pyridine / 3 h

2.1: 84 percent / ZnI₂ / CH₂Cl₂ / 20 °C

3.1: 92 percent / sodium methoxide / methanol; tetrahydrofuran / 2 h / 20 °C

4.1: 93 percent / NaH / dimethylformamide / 2 h / 0 °C

5.1: Sn(OTf)2; 4 Angstroem molecular sieves / tetrahydrofuran / 0.25 h / 20 °C

5.2: 75 percent / N-bromosuccinimide / tetrahydrofuran / 0.5 h / 0 °C

6.1: 92 percent / dimethylaminopyridine; triethylamine / CH₂Cl₂ / 2 h / 20 °C

With hydrogenchloride; dmap; tin(II) trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; sodium hydride; triethylamine; zinc(II) iodide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200300248