Technology Process of (2R,3S,4S,5S,6R)-2-(((2S,3R,4S,5R,6S)-6-(((2R,3S,4R,5S,6S)-6-(benzyloxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol
There total 8 articles about (2R,3S,4S,5S,6R)-2-(((2S,3R,4S,5R,6S)-6-(((2R,3S,4R,5S,6S)-6-(benzyloxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-4,5-dihydroxy-2-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:
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1385024-17-8
(2R,3S,4S,5S,6R)-2-(((2S,3R,4S,5R,6S)-6-(((2R,3S,4R,5S,6S)-6-(benzyloxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol
- Guidance literature:
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With
osmium(VIII) oxide; 4-methylmorpholine N-oxide;
In
water; acetone; tert-butyl alcohol;
at 0 ℃;
for 12h;
diastereoselective reaction;
DOI:10.1021/ja305321e
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1385024-17-8
(2R,3S,4S,5S,6R)-2-(((2S,3R,4S,5R,6S)-6-(((2R,3S,4R,5S,6S)-6-(benzyloxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol
- Guidance literature:
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Multi-step reaction with 4 steps
1: dmap / dichloromethane / 5 h / -78 °C
2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine / dichloromethane / 3 h / 0 °C
3: sodium tetrahydroborate / methanol / 3 h / -78 °C
4: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 12 h / 0 °C
With
dmap; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium tetrahydroborate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; triphenylphosphine;
In
methanol; dichloromethane; water; acetone; tert-butyl alcohol;
DOI:10.1021/ja305321e
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-
1385024-17-8
(2R,3S,4S,5S,6R)-2-(((2S,3R,4S,5R,6S)-6-(((2R,3S,4R,5S,6S)-6-(benzyloxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol
- Guidance literature:
-
Multi-step reaction with 5 steps
1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine / dichloromethane / 3 h / 0 °C
2: sodium tetrahydroborate / methanol; dichloromethane / 3 h / -78 °C
3: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine / dichloromethane / 3 h / 0 °C
4: sodium tetrahydroborate / methanol / 3 h / -78 °C
5: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 12 h / 0 °C
With
tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium tetrahydroborate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; triphenylphosphine;
In
methanol; dichloromethane; water; acetone; tert-butyl alcohol;
DOI:10.1021/ja305321e