Technology Process of (2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose
There total 1 articles about (2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
dmap; triethylamine;
In
dichloromethane;
at 0 - 20 ℃;
for 21.5h;
DOI:10.1021/jo051686m
- Guidance literature:
-
Methyltriphenylphosphonium bromide;
With
potassium tert-butylate;
In
toluene;
at 105 ℃;
for 1h;
(2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose;
In
toluene;
at 105 ℃;
for 2h;
DOI:10.1021/jo051686m
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: potassium tert-butoxide / toluene / 1 h / 105 °C
1.2: 97 percent / toluene / 2 h / 105 °C
2.1: 97 percent / NaH / various solvent(s); tetrahydrofuran / 4 h / 0 °C
3.1: 72 percent / acetic acid / H2O / 4.5 h / 50 °C
4.1: NaIO4 / tetrahydrofuran; H2O / 1.5 h / 20 °C
5.1: 3.04 g / tetrahydrofuran / 2 h / -20 °C
6.1: 84 percent / Grubbs' second generation catalyst / toluene / 1.5 h / 80 °C
7.1: 95 percent / H2 / Pd/C / ethyl acetate / 21 h / 20 °C
8.1: 97 percent / HCl / methanol / 120 h / 0 - 20 °C
With
hydrogenchloride; sodium periodate; potassium tert-butylate; hydrogen; sodium hydride; acetic acid;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal;
In
tetrahydrofuran; methanol; water; ethyl acetate; toluene;
1.2: Wittig reaction;
DOI:10.1021/jo051686m
