Technology Process of 3-((3aR,4R,6S,7S,7aR)-7-azido-4-(benzyloxy)-tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)propan-1-ol
There total 11 articles about 3-((3aR,4R,6S,7S,7aR)-7-azido-4-(benzyloxy)-tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)propan-1-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
tetrabutyl ammonium fluoride;
In
tetrahydrofuran;
at 20 ℃;
for 12h;
DOI:10.1021/ol0602811
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 85 percent / DMAP / CH2Cl2 / 14 h / -78 °C
2: 88 percent / Pd2(DBA)3*CHCl3; triphenylphosphine / CH2Cl2 / 2 h / 0 - 20 °C
3: 94 percent / NaBH4 / CH2Cl2; methanol / 4 h / -78 °C
4: 72 percent / pyridine; DMAP / CH2Cl2 / 24 h / 20 °C
5: 77 percent / TMSN3 / allylpalladium chloride dimer; 1,4-bis(diphenylphosphino)butane / tetrahydrofuran / 24 h / 50 °C
6: 92 percent / N-methylmorpholine N-oxide; water / OsO4 / 2-methyl-propan-2-ol; acetone / 24 h
7: 97 percent / para-toluenesulfonic acid monohydrate / acetone / 0.5 h / 0 °C
8: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
With
pyridine; dmap; sodium tetrahydroborate; trimethylsilylazide; tetrabutyl ammonium fluoride; water; 4-methylmorpholine N-oxide;
tris(dibenzylideneacetone)dipalladium(0) chloroform complex; osmium(VIII) oxide; bis(η3-allyl-μ-chloropalladium(II)); toluene-4-sulfonic acid; triphenylphosphine; 1,4-di(diphenylphosphino)-butane;
In
tetrahydrofuran; methanol; dichloromethane; acetone; tert-butyl alcohol;
3: Luche reduction;
DOI:10.1021/ol0602811
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 84 percent / NBS; H2O; NaHCO3 / NaOAc*3H2O / tetrahydrofuran / 0.5 h / 0 °C
2: 85 percent / DMAP / CH2Cl2 / 14 h / -78 °C
3: 88 percent / Pd2(DBA)3*CHCl3; triphenylphosphine / CH2Cl2 / 2 h / 0 - 20 °C
4: 94 percent / NaBH4 / CH2Cl2; methanol / 4 h / -78 °C
5: 72 percent / pyridine; DMAP / CH2Cl2 / 24 h / 20 °C
6: 77 percent / TMSN3 / allylpalladium chloride dimer; 1,4-bis(diphenylphosphino)butane / tetrahydrofuran / 24 h / 50 °C
7: 92 percent / N-methylmorpholine N-oxide; water / OsO4 / 2-methyl-propan-2-ol; acetone / 24 h
8: 97 percent / para-toluenesulfonic acid monohydrate / acetone / 0.5 h / 0 °C
9: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
With
pyridine; dmap; sodium tetrahydroborate; N-Bromosuccinimide; trimethylsilylazide; tetrabutyl ammonium fluoride; water; sodium hydrogencarbonate; 4-methylmorpholine N-oxide;
tris(dibenzylideneacetone)dipalladium(0) chloroform complex; osmium(VIII) oxide; bis(η3-allyl-μ-chloropalladium(II)); sodium acetate; toluene-4-sulfonic acid; triphenylphosphine; 1,4-di(diphenylphosphino)-butane;
In
tetrahydrofuran; methanol; dichloromethane; acetone; tert-butyl alcohol;
1: Achmatowicz reaction / 4: Luche reduction;
DOI:10.1021/ol0602811
![(3-((3aR,4R,6S,7S,7aR)-7-azido-4-(benzyloxy)-tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)propoxy)(tert-butyl)dimethylsilane](/Databaselist/images/loading.webp)
