Technology Process of (2R,3S,4R,5S,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl pivalate
There total 10 articles about (2R,3S,4R,5S,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl pivalate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
osmium(VIII) oxide; 4-methylmorpholine N-oxide;
In
water; acetone; tert-butyl alcohol;
at 0 ℃;
optical yield given as %de;
DOI:10.1039/c1cc13837e
- Guidance literature:
-
Multi-step reaction with 9 steps
1: N-Bromosuccinimide; sodium acetate; sodium hydrogencarbonate / tetrahydrofuran; water / 1 h / 0 °C
2: dmap / dichloromethane / 12 h / -78 - -30 °C
3: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine / dichloromethane / 8 h / 0 °C
4: dihydrogen peroxide; sodium hydroxide / methanol; water / 6 h / 20 °C
5: hydrazine hydrate / methanol / 0.5 h / 0 °C
6: manganese(IV) oxide / dichloromethane / 12 h / 50 °C
7: sodium tetrahydroborate; cerium(III) chloride / methanol; dichloromethane / 2 h / -78 °C
8: dmap / dichloromethane / 20 °C / Inert atmosphere
9: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 0 °C
With
dmap; manganese(IV) oxide; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium tetrahydroborate; N-Bromosuccinimide; osmium(VIII) oxide; cerium(III) chloride; dihydrogen peroxide; sodium acetate; sodium hydrogencarbonate; hydrazine hydrate; 4-methylmorpholine N-oxide; triphenylphosphine; sodium hydroxide;
In
tetrahydrofuran; methanol; dichloromethane; water; acetone; tert-butyl alcohol;
5: Wharton rearrangement / 5: Wharton rearrangement;
DOI:10.1039/c1cc13837e
- Guidance literature:
-
Multi-step reaction with 10 steps
1: (R)-RuCl(η6-mesitylene)-(S,S)-TsDPEN; sodium formate; cetyltrimethylammonim bromide; sodium hydrogencarbonate / dichloromethane; water / 24 h / 20 °C
2: N-Bromosuccinimide; sodium acetate; sodium hydrogencarbonate / tetrahydrofuran; water / 1 h / 0 °C
3: dmap / dichloromethane / 12 h / -78 - -30 °C
4: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine / dichloromethane / 8 h / 0 °C
5: dihydrogen peroxide; sodium hydroxide / methanol; water / 6 h / 20 °C
6: hydrazine hydrate / methanol / 0.5 h / 0 °C
7: manganese(IV) oxide / dichloromethane / 12 h / 50 °C
8: sodium tetrahydroborate; cerium(III) chloride / methanol; dichloromethane / 2 h / -78 °C
9: dmap / dichloromethane / 20 °C / Inert atmosphere
10: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 0 °C
With
dmap; manganese(IV) oxide; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium tetrahydroborate; N-Bromosuccinimide; osmium(VIII) oxide; cerium(III) chloride; (R)-RuCl(η6-mesitylene)-(S,S)-TsDPEN; dihydrogen peroxide; sodium formate; sodium acetate; cetyltrimethylammonim bromide; sodium hydrogencarbonate; hydrazine hydrate; 4-methylmorpholine N-oxide; triphenylphosphine; sodium hydroxide;
In
tetrahydrofuran; methanol; dichloromethane; water; acetone; tert-butyl alcohol;
6: Wharton rearrangement / 6: Wharton rearrangement;
DOI:10.1039/c1cc13837e
