3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate

Base Information

Chemical Name:3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate
CAS No.:678159-06-3
Molecular Formula:C₂₃H₂₃Cl₃N₂O₈
Molecular Weight:561.803
Hs Code.:

Synonyms:3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate

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Chemical Property of 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate

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Technology Process of 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate

There total 11 articles about 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-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:

: 545-06-2
trichloroacetonitrile

: 678159-10-9
3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranose

: 678159-06-3
3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate

Guidance literature:: With 4 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/jo035583k

Reference yield:

: 766-39-2
2,3-Dimethylmaleic anhydride

: 678159-06-3
3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 9 steps

1: 68 percent / N₂H₄*AcOH

2: 78 percent / imidazole

3: 73 percent / NaOMe

4: 91 percent / TsOH

5: 85 percent / pyridine / CH₂Cl₂ / 20 °C

6: 63 percent / TBAF; AcOH / tetrahydrofuran; ethyl acetate / 0.5 h / -10 °C

7: 1,8-diazabicyclo[5.4.0]undec-7-ene; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

With pyridine; 1H-imidazole; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; hydrazinium monoacetate; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1021/jo035583k

Reference yield:

: 90-76-6,90-77-7,530-23-4,579-32-8,579-33-9,643-68-5,2596-19-2,6490-68-2,6490-70-6,6490-72-8,6490-73-9,6490-74-0,14196-84-0,14196-86-2,14257-69-3,58381-21-8
2-deoxy-2-amino glucose

: 678159-06-3
3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 9 steps

1: 68 percent / N₂H₄*AcOH

2: 78 percent / imidazole

3: 73 percent / NaOMe

4: 91 percent / TsOH

5: 85 percent / pyridine / CH₂Cl₂ / 20 °C

6: 63 percent / TBAF; AcOH / tetrahydrofuran; ethyl acetate / 0.5 h / -10 °C

7: 1,8-diazabicyclo[5.4.0]undec-7-ene; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

With pyridine; 1H-imidazole; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; hydrazinium monoacetate; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1021/jo035583k