4-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranosyl trichloroacetimidate

Base Information

Chemical Name:4-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranosyl trichloroacetimidate
CAS No.:385421-86-3
Molecular Formula:C₂₈H₃₁Cl₃N₂O₁₀
Molecular Weight:661.921
Hs Code.:

Synonyms:4-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranosyl trichloroacetimidate

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Chemical Property of 4-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranosyl trichloroacetimidate

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Technology Process of 4-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranosyl trichloroacetimidate

There total 10 articles about 4-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-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: 70.0%

: 545-06-2
trichloroacetonitrile

: 385422-20-8
4-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranoside

: 385421-86-3
4-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 2h;
DOI:10.1021/jo015987h

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 385421-86-3
4-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 91 percent / tetrafluoroboric acid / dimethylformamide / 5 h

2.1: DIPC; DMAP / CH₂Cl₂ / 0 °C

2.2: 92 percent / CH₂Cl₂ / 12 h / 20 °C

3.1: 70 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

4.1: 100 percent / DMAP / CH₂Cl₂ / 0.5 h

5.1: TBAF; acetic acid / tetrahydrofuran / 1.5 h / 20 °C

6.1: 70 percent / DBU / CH₂Cl₂ / 2 h

With triethylsilane; dmap; tetrafluoroboric acid; bis-2-propyl carbonate; tetrabutyl ammonium fluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo015987h

Reference yield:

: 315208-18-5
3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside

: 385421-86-3
4-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 85 percent / imidazole / CH₂Cl₂ / 1.5 h

2.1: 100 percent / sodium methoxide / methanol / 2 h

3.1: 91 percent / tetrafluoroboric acid / dimethylformamide / 5 h

4.1: DIPC; DMAP / CH₂Cl₂ / 0 °C

4.2: 92 percent / CH₂Cl₂ / 12 h / 20 °C

5.1: 70 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

6.1: 100 percent / DMAP / CH₂Cl₂ / 0.5 h

7.1: TBAF; acetic acid / tetrahydrofuran / 1.5 h / 20 °C

8.1: 70 percent / DBU / CH₂Cl₂ / 2 h

With 1H-imidazole; triethylsilane; dmap; tetrafluoroboric acid; bis-2-propyl carbonate; tetrabutyl ammonium fluoride; sodium methylate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo015987h