Technology Process of (2RS,4R,5S,6R,7R,8R)-N4-benzyl-N4-acetyl-1,5-bis(benzyloxy)-6,7:8,9-di-O-isopropylidenenonan-2-ol
There total 9 articles about (2RS,4R,5S,6R,7R,8R)-N4-benzyl-N4-acetyl-1,5-bis(benzyloxy)-6,7:8,9-di-O-isopropylidenenonan-2-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(2RS,4R,5S,6R,7R,8R)-N4-benzyl-N4-acetyl-5-benzyloxy-6,7:8,9-di-O-isopropylidenenonane-1,2-diol;
With
di(n-butyl)tin oxide;
In
methanol; toluene;
at 85 ℃;
for 2h;
benzyl bromide;
With
tetrabutylammomium bromide;
In
toluene;
at 80 ℃;
for 10h;
DOI:10.1021/jo034679b
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 74 percent / Ag2O / CH2Cl2
2.1: 87 percent / LiAlH4 / tetrahydrofuran
3.1: 83 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h
4.1: MgSO4 / tetrahydrofuran / 2 h / 20 °C
5.1: 1.31 g / tetrahydrofuran / 2 h / 20 °C
6.1: 88 percent / Et3N; DMAP / CH2Cl2 / 8 h / 20 °C
7.1: 76 percent / aq. NMO; OsO4 / acetone; butan-1-ol / 19 h / 20 °C
8.1: Bu2SnO / toluene; methanol / 2 h / 85 °C
8.2: 98 percent / TBAB / toluene / 10 h / 80 °C
With
dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; di(n-butyl)tin oxide; magnesium sulfate; Dess-Martin periodane; triethylamine; silver(l) oxide;
In
tetrahydrofuran; methanol; dichloromethane; acetone; toluene; butan-1-ol;
DOI:10.1021/jo034679b
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 87 percent / LiAlH4 / tetrahydrofuran
2.1: 83 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h
3.1: MgSO4 / tetrahydrofuran / 2 h / 20 °C
4.1: 1.31 g / tetrahydrofuran / 2 h / 20 °C
5.1: 88 percent / Et3N; DMAP / CH2Cl2 / 8 h / 20 °C
6.1: 76 percent / aq. NMO; OsO4 / acetone; butan-1-ol / 19 h / 20 °C
7.1: Bu2SnO / toluene; methanol / 2 h / 85 °C
7.2: 98 percent / TBAB / toluene / 10 h / 80 °C
With
dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; di(n-butyl)tin oxide; magnesium sulfate; Dess-Martin periodane; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; acetone; toluene; butan-1-ol;
DOI:10.1021/jo034679b
