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

Base Information

Chemical Name:4-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranoside
CAS No.:385422-20-8
Molecular Formula:C₂₆H₃₁NO₁₀
Molecular Weight:517.533
Hs Code.:

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

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

Chemical Property:

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

There total 9 articles about 4-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-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:

: 385421-85-2
tert-butyldimethylsilyl 4-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranoside

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

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 1.5h;
DOI:10.1021/jo015987h

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

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

Guidance literature:: Multi-step reaction with 5 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

With triethylsilane; dmap; tetrafluoroboric acid; bis-2-propyl carbonate; tetrabutyl ammonium fluoride; acetic acid; 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

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

Guidance literature:: Multi-step reaction with 7 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

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