O-(4-O-levulinyl-2,3-di-O-methyl-β-D-glucopyranosyluronic acid)-(1->4)-3-O-acetyl-1,6-anhydro-2-O-benzyl-β-D-glucopyranose

Base Information

Chemical Name:O-(4-O-levulinyl-2,3-di-O-methyl-β-D-glucopyranosyluronic acid)-(1->4)-3-O-acetyl-1,6-anhydro-2-O-benzyl-β-D-glucopyranose
CAS No.:189390-31-6
Molecular Formula:C₂₈H₃₆O₁₄
Molecular Weight:596.585
Hs Code.:

Synonyms:O-(4-O-levulinyl-2,3-di-O-methyl-β-D-glucopyranosyluronic acid)-(1->4)-3-O-acetyl-1,6-anhydro-2-O-benzyl-β-D-glucopyranose

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Chemical Property of O-(4-O-levulinyl-2,3-di-O-methyl-β-D-glucopyranosyluronic acid)-(1->4)-3-O-acetyl-1,6-anhydro-2-O-benzyl-β-D-glucopyranose

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Technology Process of O-(4-O-levulinyl-2,3-di-O-methyl-β-D-glucopyranosyluronic acid)-(1->4)-3-O-acetyl-1,6-anhydro-2-O-benzyl-β-D-glucopyranose

There total 8 articles about O-(4-O-levulinyl-2,3-di-O-methyl-β-D-glucopyranosyluronic acid)-(1->4)-3-O-acetyl-1,6-anhydro-2-O-benzyl-β-D-glucopyranose 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:

: 189390-30-5
O-[4-O-levulinyl-2,3-di-O-methyl-6-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl]-(1->4)-3-O-acetyl-1,6-anhydro-2-O-benzyl-β-D-glucopyranose

: 189390-31-6
O-(4-O-levulinyl-2,3-di-O-methyl-β-D-glucopyranosyluronic acid)-(1->4)-3-O-acetyl-1,6-anhydro-2-O-benzyl-β-D-glucopyranose

Guidance literature:: With chromium(VI) oxide; sulfuric acid; In acetone; at 0 ℃; for 3h;
DOI:10.1021/jm960726z

Reference yield:

: 40608-06-8
levulinic anhydride

: 189390-31-6
O-(4-O-levulinyl-2,3-di-O-methyl-β-D-glucopyranosyluronic acid)-(1->4)-3-O-acetyl-1,6-anhydro-2-O-benzyl-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 2 steps

1: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h

2: CrO₃, aq. H₂SO₄ / acetone / 3 h / 0 °C

With chromium(VI) oxide; dmap; sulfuric acid; triethylamine; In dichloromethane; acetone;
DOI:10.1021/jm960726z

Reference yield:

: 189390-26-9
O-(4,6-isopropylidene-2,3-di-O-methyl-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose

: 189390-31-6
O-(4-O-levulinyl-2,3-di-O-methyl-β-D-glucopyranosyluronic acid)-(1->4)-3-O-acetyl-1,6-anhydro-2-O-benzyl-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 6 steps

1: sodium benzylate / 4 h / 80 °C

2: 23.4 g / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h

3: 21.6 g / aq. CF₃CO₂H / CH₂Cl₂ / 0.67 h / Ambient temperature

4: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 50 °C

5: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h

6: CrO₃, aq. H₂SO₄ / acetone / 3 h / 0 °C

With chromium(VI) oxide; sodium benzoate; dmap; sulfuric acid; triethylamine; trifluoroacetic acid; In dichloromethane; acetone;
DOI:10.1021/jm960726z