1-(2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranos-1-yl)-1H-indole-3-carbaldehyde

Base Information

Chemical Name:1-(2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranos-1-yl)-1H-indole-3-carbaldehyde
CAS No.:881909-51-9
Molecular Formula:C₄₃H₄₁NO₆
Molecular Weight:667.802
Hs Code.:

Synonyms:1-(2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranos-1-yl)-1H-indole-3-carbaldehyde

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Chemical Property of 1-(2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranos-1-yl)-1H-indole-3-carbaldehyde

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Technology Process of 1-(2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranos-1-yl)-1H-indole-3-carbaldehyde

There total 6 articles about 1-(2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranos-1-yl)-1H-indole-3-carbaldehyde 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: 89.0%

: 68-12-2,33513-42-7
N,N-dimethyl-formamide

: 4196-37-6
1-(2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranos-1-yl)-1H-indole

: 881909-51-9
1-(2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranos-1-yl)-1H-indole-3-carbaldehyde

Guidance literature:: N,N-dimethyl-formamide; 1-(2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranos-1-yl)-1H-indole; With trichlorophosphate; at 0 - 35 ℃; for 2h; Inert atmosphere;

With sodium hydroxide; In water; N,N-dimethyl-formamide; at 100 ℃; for 0.5h;
DOI:10.1016/j.tet.2018.01.017

Reference yield:

: 487-89-8,1228547-52-1
Indole-3-carboxaldehyde

: 25320-59-6
tetra-O-benzyl glucopyranosyl chloride

: 881909-51-9
1-(2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranos-1-yl)-1H-indole-3-carbaldehyde

Guidance literature:: Indole-3-carboxaldehyde; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.333333h;

tetra-O-benzyl glucopyranosyl chloride; In N,N-dimethyl-formamide; at 0 - 20 ℃;

Reference yield:

: 50-99-7
D-glucose

: 881909-51-9
1-(2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranos-1-yl)-1H-indole-3-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1.1: ethanol; water / 24 h / Reflux

2.1: sodium hydride / tetrahydrofuran; mineral oil / 17 h / 0 °C / Reflux

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / ethyl acetate / 0.75 h / 20 °C

4.1: trichlorophosphate / 2 h / 0 - 35 °C / Inert atmosphere

4.2: 0.5 h / 100 °C

With sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; trichlorophosphate; In tetrahydrofuran; ethanol; water; ethyl acetate; mineral oil;
DOI:10.1016/j.tet.2018.01.017