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

Base Information

• Chemical Name: 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
• CAS No.: 121924-79-6
• Molecular Formula: C₃₂H₃₈O₁₈S
• Molecular Weight: 742.709
• Mol file: 121924-79-6.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 3 articles about 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 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: 81.0%

methyl (1S,4aS,8R,9S,9aS)-8-hydroxymethyl-6-oxo-1-(2',3',4',6'-tetraacetyl-β-D-glucopyranosyloxy)-1,4a,5,6,8,8a-hexahydropyrano<3,4-c>pyran-4-carboxylate (121911-99-7) + p-toluenesulfonyl chloride (98-59-9) → 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:

With dmap; In pyridine; for 12h; Ambient temperature;

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

Reference yield:

O,O,O,O-tetraacetylsecologaninn (27856-66-2) → 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 3 steps

1: 42 percent / osmium tetroxide, potassium chlorate / dioxane; H₂O / 90 °C

2: 59 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 32 h / Ambient temperature

3: 81 percent / dimethylaminopyridine / pyridine / 12 h / Ambient temperature

With dmap; osmium(VIII) oxide; potassium chlorate; sodium acetate; pyridinium chlorochromate; In 1,4-dioxane; pyridine; dichloromethane; water;

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

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:

methyl (1S,4aS,8R,9S,9aS)-8-hydroxymethyl-6-oxo-1-(2',3',4',6'-tetraacetyl-β-D-glucopyranosyloxy)-1,4a,5,6,8,8a-hexahydropyrano<3,4-c>pyran-4-carboxylate

p-toluenesulfonyl chloride

O,O,O,O-tetraacetylsecologaninn

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