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

Base Information

• Chemical Name: 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
• CAS No.: 102436-08-8
• Molecular Formula: C₂₅H₃₄O₁₆
• Molecular Weight: 590.535
• Mol file: 102436-08-8.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 2 articles about 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 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: 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;

Reference yield:

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) → methyl (1S,4aS,8S,8aS)-6-oxo-1-(2',3',4',6'-tetraacetyl-β-D-glucopyranosyloxy)-8-tosyloxymethyl-1,4a,5,6,8,8a-hexahydro-pyrano<3,4-c>pyran-4-carboxylate (121924-79-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 59 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 32 h / Ambient temperature

2: 81 percent / dimethylaminopyridine / pyridine / 12 h / Ambient temperature

With dmap; sodium acetate; pyridinium chlorochromate; In pyridine; dichloromethane;

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

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

Downstream raw materials:

secogalioside

methyl (1S,4aS,8S,8aS)-6-oxo-1-(2',3',4',6'-tetraacetyl-β-D-glucopyranosyloxy)-8-tosyloxymethyl-1,4a,5,6,8,8a-hexahydro-pyrano<3,4-c>pyran-4-carboxylate