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

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Chemical Name: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
CAS No.:189390-30-5
Molecular Formula:C₃₄H₅₂O₁₃Si
Molecular Weight:696.865
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 6 articles about 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 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:

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

: 189390-30-5
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

Guidance literature:: Multi-step reaction with 5 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

With sodium benzoate; dmap; triethylamine; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/jm960726z

Reference yield:

: 189390-27-0
O-(4,6-isopropylidene-2,3-di-O-methyl-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2-O-benzyl-β-D-glucopyranose

: 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

Guidance literature:: Multi-step reaction with 4 steps

1: 23.4 g / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h

2: 21.6 g / aq. CF₃CO₂H / CH₂Cl₂ / 0.67 h / Ambient temperature

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

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

With dmap; triethylamine; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/jm960726z

Reference yield:

: 189390-29-2
O-(2,3-di-O-methyl-β-D-glucopyranosyl)-(1->4)-3-O-acetyl-1,6-anhydro-2-O-benzyl-β-D-glucopyranose

: 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

Guidance literature:: Multi-step reaction with 2 steps

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

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

With dmap; triethylamine; In dichloromethane;
DOI:10.1021/jm960726z