4,6-O-benzylidene-2,3-bis(tert-butyldimethylsilyl)-β-D-glukopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 4,6-O-benzylidene-2,3-bis(tert-butyldimethylsilyl)-β-D-glukopyranosyl trichloroacetimidate
• CAS No.: 292140-11-5
• Molecular Formula: C₂₇H₄₄Cl₃NO₆Si₂
• Molecular Weight: 641.179

Synonyms:4,6-O-benzylidene-2,3-bis(tert-butyldimethylsilyl)-β-D-glukopyranosyl trichloroacetimidate

Chemical Property of 4,6-O-benzylidene-2,3-bis(tert-butyldimethylsilyl)-β-D-glukopyranosyl trichloroacetimidate

Chemical Property:

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Technology Process of 4,6-O-benzylidene-2,3-bis(tert-butyldimethylsilyl)-β-D-glukopyranosyl trichloroacetimidate

There total 4 articles about 4,6-O-benzylidene-2,3-bis(tert-butyldimethylsilyl)-β-D-glukopyranosyl trichloroacetimidate 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: 90.0%

4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-D-glucopyranose (113533-88-3,113533-89-4) + trichloroacetonitrile (545-06-2) → 4,6-O-benzylidene-2,3-bis(tert-butyldimethylsilyl)-β-D-glukopyranosyl trichloroacetimidate (292140-11-5)

Guidance literature:

With sodium hydride; In benzene; for 4h;

DOI:10.1021/ja001013f

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 4,6-O-benzylidene-2,3-bis(tert-butyldimethylsilyl)-β-D-glukopyranosyl trichloroacetimidate (292140-11-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / lutidine / CH₂Cl₂ / 4 h / 20 °C

2: 88 percent / H₂O / tetrahydrofuran; ethanol / 10 h / 20 °C / UV-irradiation

3: 90 percent / NaH / benzene / 4 h

With lutidine; water; sodium hydride; In tetrahydrofuran; ethanol; dichloromethane; benzene;

DOI:10.1021/ja001013f

Reference yield:

ortho-nitrobenzyl 4,6-O-benzylidene-β-D-glucopyranoside → 4,6-O-benzylidene-2,3-bis(tert-butyldimethylsilyl)-β-D-glukopyranosyl trichloroacetimidate (292140-11-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / lutidine / CH₂Cl₂ / 4 h / 20 °C

2: 88 percent / H₂O / tetrahydrofuran; ethanol / 10 h / 20 °C / UV-irradiation

3: 90 percent / NaH / benzene / 4 h

With lutidine; water; sodium hydride; In tetrahydrofuran; ethanol; dichloromethane; benzene;

DOI:10.1021/ja001013f

upstream raw materials:

4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-D-glucopyranose

trichloroacetonitrile

t-butyldimethylsiyl triflate

1-O-(o-nitrobenzyl)-4,6-O-benzylidene-2,3-bis(tert-butyldimethylsilyl)-β-D-glucopyranoside

Downstream raw materials:

1-O-(3,4,5-tri-benzylgalloyl)-4,6-benzylidene-2,3-bis-(tert-butyldimethylsilyl)-β-D-glucopyranoside

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