tert-butyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranoside

Base Information

Chemical Name:tert-butyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranoside
CAS No.:385422-23-1
Molecular Formula:C₃₀H₄₁NO₉Si
Molecular Weight:587.742
Hs Code.:

Synonyms:tert-butyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranoside

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Chemical Property of tert-butyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranoside

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Technology Process of tert-butyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranoside

There total 7 articles about tert-butyldimethylsilyl 4,6-O-benzylidene-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: 92.0%

: 123-76-2
levulinic acid

: 216877-67-7
tert-butyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside

: 385422-23-1
tert-butyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranoside

Guidance literature:: levulinic acid; With dmap; bis-2-propyl carbonate; In dichloromethane; at 0 ℃;

tert-butyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside; In dichloromethane; at 20 ℃; for 12h; Further stages.;
DOI:10.1021/jo015987h

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 385422-23-1
tert-butyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 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

With dmap; tetrafluoroboric acid; bis-2-propyl carbonate; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo015987h

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 385422-23-1
tert-butyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleoyl-3-O-levulinyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; dmap; tetrafluoroboric acid; bis-2-propyl carbonate; sodium methylate; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo015987h