Methyl (1S,4aS,6R,9S,9aS)-4a,5,6,8,9,9a-hexahydro-1-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-6,9-epoxy-1H-pyrano<3,4-d>oxepine-4-carboxylate

Base Information

• Chemical Name: Methyl (1S,4aS,6R,9S,9aS)-4a,5,6,8,9,9a-hexahydro-1-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-6,9-epoxy-1H-pyrano<3,4-d>oxepine-4-carboxylate
• CAS No.: 79409-49-7
• Molecular Formula: C₂₅H₃₂O₁₅
• Molecular Weight: 572.52

Synonyms:Methyl (1S,4aS,6R,9S,9aS)-4a,5,6,8,9,9a-hexahydro-1-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-6,9-epoxy-1H-pyrano<3,4-d>oxepine-4-carboxylate

Chemical Property of Methyl (1S,4aS,6R,9S,9aS)-4a,5,6,8,9,9a-hexahydro-1-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-6,9-epoxy-1H-pyrano<3,4-d>oxepine-4-carboxylate

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Technology Process of Methyl (1S,4aS,6R,9S,9aS)-4a,5,6,8,9,9a-hexahydro-1-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-6,9-epoxy-1H-pyrano<3,4-d>oxepine-4-carboxylate

There total 3 articles about Methyl (1S,4aS,6R,9S,9aS)-4a,5,6,8,9,9a-hexahydro-1-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-6,9-epoxy-1H-pyrano<3,4-d>oxepine-4-carboxylate 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: 39.0%

Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-3,4-dihydro-2-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-3-vinyl-2H-pyran-5-carboxylate (79409-46-4) → 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3) + Methyl (2S,3S,4S,9S)-3-(1,2-dihydroxyethyl)-4-(1,3-dioxolan-2-ylmethyl)-3,4-dihydro-2-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-2H-pyran-5-carboxylate (79409-47-5) + Methyl (1S,4aS,6R,9S,9aS)-4a,5,6,8,9,9a-hexahydro-1-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-6,9-epoxy-1H-pyrano<3,4-d>oxepine-4-carboxylate (79409-49-7)

Guidance literature:

With osmium(VIII) oxide; In pyridine; at 20 ℃; for 72h;

Reference yield: 17.0%

O,O,O,O-tetraacetylsecologaninn (27856-66-2) → 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3) + Methyl (1S,4aS,6R,9S,9aS)-4a,5,6,8,9,9a-hexahydro-1-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-6,9-epoxy-1H-pyrano<3,4-d>oxepine-4-carboxylate (79409-49-7) + methyl (1S,4aS,6RS,8S,8aS)-6-hydroxy-8-hydroxymethyl-1-(2',3',4',6'-tetraacetyl-β-D-glucopyranosyloxy)-1,4a,5,6,8,8a-hexahydro-pyrano<3,4-c>pyran-4-carboxylate (102436-08-8,121961-12-4,121961-13-5)

Guidance literature:

With osmium(VIII) oxide; potassium chlorate; In 1,4-dioxane; water; at 90 ℃;

DOI:10.1016/S0040-4020(01)86082-8

Reference yield: 2.6%

Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-3,4-dihydro-2-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-3-vinyl-2H-pyran-5-carboxylate (79409-46-4) → 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3) + Methyl (2S,3S,4S,9S)-3-(1,2-dihydroxyethyl)-4-(1,3-dioxolan-2-ylmethyl)-3,4-dihydro-2-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-2H-pyran-5-carboxylate (79409-47-5) + Methyl (1S,4aS,6R,9S,9aS)-4a,5,6,8,9,9a-hexahydro-1-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-6,9-epoxy-1H-pyrano<3,4-d>oxepine-4-carboxylate (79409-49-7) + Methyl (1S,4aS,6RS,8S,8aS)-1,4a,5,6,8,8a-hexahydro-6-hydroxy-8-(hydroxymethyl)-1-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)pyrano<3,4-c>pyran-4-carboxylate (102436-08-8)

Guidance literature:

With osmium(VIII) oxide; In pyridine; at 20 ℃; for 72h;

upstream raw materials:

O,O,O,O-tetraacetylsecologaninn

Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-3,4-dihydro-2-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-3-vinyl-2H-pyran-5-carboxylate

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