O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate

Base Information

Chemical Name:O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate
CAS No.:310870-37-2
Molecular Formula:C₂₂H₂₁Cl₃N₄O₅
Molecular Weight:527.792
Hs Code.:

Synonyms:O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate

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Chemical Property of O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate

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Technology Process of O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate

There total 13 articles about O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α,β-D-glucopyranosyl) 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: 95.0%

: 545-06-2
trichloroacetonitrile

: 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α,β-D-glucopyranose

: 310870-37-2
O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 3h;
DOI:10.1002/ejoc.200300210

Reference yield:

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

: 310870-37-2
O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 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: 85 percent / NaH; TBAI / CH₂Cl₂ / 24 h

5: 100 percent / AcOH; TBAF / tetrahydrofuran / -40 °C

6: 95 percent / DBU / CH₂Cl₂ / 2 h

With 1H-imidazole; dmap; triflic azide; tetrabutyl ammonium fluoride; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/b418041k

Reference yield:

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

: 310870-37-2
O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / NaH; TBAI / CH₂Cl₂ / 24 h

2: 100 percent / AcOH; TBAF / tetrahydrofuran / -40 °C

3: 95 percent / DBU / CH₂Cl₂ / 2 h

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane;
DOI:10.1039/b418041k