tert-butyldimethylsilyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-p-methoxybenzyl-β-D-glucopyranoside

Base Information

Chemical Name:tert-butyldimethylsilyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-p-methoxybenzyl-β-D-glucopyranoside
CAS No.:850428-22-7
Molecular Formula:C₂₇H₃₇N₃O₆Si
Molecular Weight:527.693
Hs Code.:

Synonyms:tert-butyldimethylsilyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-p-methoxybenzyl-β-D-glucopyranoside

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Chemical Property of tert-butyldimethylsilyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-p-methoxybenzyl-β-D-glucopyranoside

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Technology Process of tert-butyldimethylsilyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-p-methoxybenzyl-β-D-glucopyranoside

There total 4 articles about tert-butyldimethylsilyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-p-methoxybenzyl-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: 70.0%

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 138923-10-1
2-azido-4,6-O-benzylidene-2-deoxyl-1-O-tert-butyldimethylsilyl-β-D-glucopyranoside

: 850428-22-7
tert-butyldimethylsilyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-p-methoxybenzyl-β-D-glucopyranoside

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 18h;
DOI:10.1039/b418041k

Reference yield:

: 2-azido-2-deoxy-D-glucose

: 850428-22-7
tert-butyldimethylsilyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-p-methoxybenzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: p-TsOH / dimethylformamide / 48 h / 40 °C

2: 70 percent / imidazole / CH₂Cl₂ / 2 h / -10 °C

3: 70 percent / BF₃*OEt₂; 4 Angstroem molecular sieves / CH₂Cl₂ / 18 h / 0 - 20 °C

With 1H-imidazole; 4 A molecular sieve; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/b418041k

Reference yield:

: 1078691-95-8
(+)-D-glucosamine hydrochloride

: 850428-22-7
tert-butyldimethylsilyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-p-methoxybenzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: MeONa; TfN₃; DMAP / methanol / 48 h

2: p-TsOH / dimethylformamide / 48 h / 40 °C

3: 70 percent / imidazole / CH₂Cl₂ / 2 h / -10 °C

4: 70 percent / BF₃*OEt₂; 4 Angstroem molecular sieves / CH₂Cl₂ / 18 h / 0 - 20 °C

With 1H-imidazole; dmap; 4 A molecular sieve; triflic azide; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/b418041k