(2R,3S,4S,5S,6R)-2-(((2R,3R,4R,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol

Base Information

Chemical Name:(2R,3S,4S,5S,6R)-2-(((2R,3R,4R,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol
CAS No.:1428345-59-8
Molecular Formula:C₁₉H₂₈O₉
Molecular Weight:400.426
Hs Code.:

Synonyms:(2R,3S,4S,5S,6R)-2-(((2R,3R,4R,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol

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Chemical Property of (2R,3S,4S,5S,6R)-2-(((2R,3R,4R,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol

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Technology Process of (2R,3S,4S,5S,6R)-2-(((2R,3R,4R,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol

There total 7 articles about (2R,3S,4S,5S,6R)-2-(((2R,3R,4R,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol 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: 98.0%

: 1428345-58-7
(2R,3S,4S,5S,6R)-2-(((2R,3R,4αS,5S,7R,8R,8αR)-7-(benzyloxy)-2,3-dimethoxy-2,3,5-trimethylhexahydro-2H-pyrano-[3,4-b]-[1,4]dioxin-8-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol

: 1428345-59-8
(2R,3S,4S,5S,6R)-2-(((2R,3R,4R,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: With trifluoroacetic acid; In dichloromethane; water; at 20 ℃; for 4h;
DOI:10.1016/j.tet.2013.02.073

Reference yield:

: 1428345-57-6
(2R,3S,6R)-6-(((2R,3R,4αS,5S,7R,8R,8αR)-7-(benzyloxy)-2,3-dimethoxy-2,3,5-trimethylhexahydro-2H-pyrano[3,4b]-[1,4]-dioxin-8-yl)oxy)-2-methyl-3,6-dihydro-2H-pyran-3-ol

: 1428345-59-8
(2R,3S,4S,5S,6R)-2-(((2R,3R,4R,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 2 steps

1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tert-butyl alcohol; acetone; water / 12 h / 0 °C

2: trifluoroacetic acid / dichloromethane; water / 4 h / 20 °C

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; trifluoroacetic acid; In dichloromethane; water; acetone; tert-butyl alcohol;
DOI:10.1016/j.tet.2013.02.073

Reference yield:

: 679412-06-7
tert-butyl ((2R,6R)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate

: 1428345-59-8
(2R,3S,4S,5S,6R)-2-(((2R,3R,4R,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 4 steps

1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine / dichloromethane / 4 h / 0 °C / Inert atmosphere

2: sodium tetrahydroborate; cerium(III) chloride / dichloromethane; methanol / 2 h / -78 °C

3: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tert-butyl alcohol; acetone; water / 12 h / 0 °C

4: trifluoroacetic acid / dichloromethane; water / 4 h / 20 °C

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; osmium(VIII) oxide; cerium(III) chloride; 4-methylmorpholine N-oxide; triphenylphosphine; trifluoroacetic acid; In methanol; dichloromethane; water; acetone; tert-butyl alcohol; 2: |Luche Cerium Reduction;
DOI:10.1016/j.tet.2013.02.073