methyl 4α-<(6β-(4-(p-acetoxyphenyl)butyl)-3,4,5,6-tetrahydro-2H-pyran-2α-yl)methyl>-3α-ethyl-3,4-dihydro-2β-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-2H-pyran-5-carboxylate

Base Information

Chemical Name:methyl 4α-<(6β-(4-(p-acetoxyphenyl)butyl)-3,4,5,6-tetrahydro-2H-pyran-2α-yl)methyl>-3α-ethyl-3,4-dihydro-2β-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-2H-pyran-5-carboxylate
CAS No.:80839-85-6
Molecular Formula:C₄₁H₅₆O₁₆
Molecular Weight:804.886
Hs Code.:

methyl 4α-<(6β-(4-(p-acetoxyphenyl)butyl)-3,4,5,6-tetrahydro-2H-pyran-2α-yl)methyl>-3α-ethyl-3,4-dihydro-2β-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-2H-pyran-5-carboxylate

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Chemical Property of methyl 4α-<(6β-(4-(p-acetoxyphenyl)butyl)-3,4,5,6-tetrahydro-2H-pyran-2α-yl)methyl>-3α-ethyl-3,4-dihydro-2β-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-2H-pyran-5-carboxylate

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Technology Process of methyl 4α-<(6β-(4-(p-acetoxyphenyl)butyl)-3,4,5,6-tetrahydro-2H-pyran-2α-yl)methyl>-3α-ethyl-3,4-dihydro-2β-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-2H-pyran-5-carboxylate

There total 11 articles about methyl 4α-<(6β-(4-(p-acetoxyphenyl)butyl)-3,4,5,6-tetrahydro-2H-pyran-2α-yl)methyl>-3α-ethyl-3,4-dihydro-2β-(2,3,4,6-tetra-O-acetyl-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:

: 74473-94-2,96038-76-5
hydrangenoside A pentaacetate

: 80839-85-6,81446-57-3,96038-79-8
methyl 4α-<(6β-(4-(p-acetoxyphenyl)butyl)-3,4,5,6-tetrahydro-2H-pyran-2α-yl)methyl>-3α-ethyl-3,4-dihydro-2β-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-2H-pyran-5-carboxylate

Guidance literature:: DOI:10.1248/cpb.29.3421

Reference yield:

: methyl 4α-<(6β-(4-(p-acetoxyphenyl)-2-hydroxybutyl)-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2α-yl)methyl>-3α-ethenyl-3,4-dihydro-2β-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-2H-pyran-5-carboxylate

: 80839-85-6,81446-57-3,96038-79-8
methyl 4α-<(6β-(4-(p-acetoxyphenyl)butyl)-3,4,5,6-tetrahydro-2H-pyran-2α-yl)methyl>-3α-ethyl-3,4-dihydro-2β-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-2H-pyran-5-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / 4 °C

2: 1.) 2,6-dimethylpyridine; 2.) H₂/Pd/C / 1.) 170 deg C, 4 h; 2.) AcOH, 60 deg C, 1 h

With 2,6-dimethylpyridine; palladium on activated charcoal; hydrogen; In pyridine;
DOI:10.1002/hlca.19840670812

Reference yield:

: 74473-94-2,96038-76-5
hydrangenoside B pentaacetate

: 80839-85-6,81446-57-3,96038-79-8
(4S,5R,6S)-4-{(2S,6S)-6-[4-(4-Acetoxy-phenyl)-butyl]-tetrahydro-pyran-2-ylmethyl}-5-ethyl-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

Guidance literature:: Multi-step reaction with 3 steps

1: NaBH₄ / tetrahydrofuran; H₂O / 70 h / Ambient temperature

2: pyridine / 4 °C

3: 1.) 2,6-dimethylpyridine; 2.) H₂/Pd/C / 1.) 170 deg C, 4 h; 2.) AcOH, 60 deg C, 1 h

With 2,6-dimethylpyridine; sodium tetrahydroborate; palladium on activated charcoal; hydrogen; In tetrahydrofuran; pyridine; water;
DOI:10.1002/hlca.19840670812