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

Base Information

• Chemical Name: 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
• CAS No.: 79409-47-5
• Molecular Formula: C₂₇H₃₈O₁₇
• Molecular Weight: 634.589

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 2 articles about 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 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: 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: 85.0%

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) + p-toluenesulfonyl chloride (98-59-9) → methyl (2S,3S,4S,9S)-3-(1-hydroxy-2-tosyloxyethyl)-4-(1,3-dioxolan-2-yl-methyl)-2-(2',3',4',6'-tetraacetyl-β-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-5-carboxylate (121924-80-9)

Guidance literature:

With dmap; In pyridine; for 4h; Ambient temperature;

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

upstream raw materials:

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:

methyl (2S,3S,4S,9S)-3-(1-hydroxy-2-tosyloxyethyl)-4-(1,3-dioxolan-2-yl-methyl)-2-(2',3',4',6'-tetraacetyl-β-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-5-carboxylate

(4S,5S,6S)-5-[(S)-1-Acetoxy-2-(toluene-4-sulfonyloxy)-ethyl]-4-[1,3]dioxolan-2-ylmethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

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