Technology Process of (4S,5S)-2-azido-6-(4-tert-butoxyphenyl)-4-(4-tert-butoxy-2-oxoethoxy)hexane-1,2-diol
There total 9 articles about (4S,5S)-2-azido-6-(4-tert-butoxyphenyl)-4-(4-tert-butoxy-2-oxoethoxy)hexane-1,2-diol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: N-methylmorpholine; isobutyl chloroformate / CH2Cl2 / 0.25 h / -20 °C
1.2: 85 percent / CH2Cl2 / 3 h / 20 °C
2.1: 80 percent / tetrahydrofuran / 4 h / -78 °C
3.1: 14 percent / K-Selectride / tetrahydrofuran / 4 h / -78 °C
4.1: 75 percent / KOH / H2O; ethanol / 5 h / Heating
5.1: 85 percent / 4-(dimethylamino)pyridine; CuSO4; triflyl azide / CH2Cl2 / 2 h
6.1: NaOH; NBu4HSO4 / benzene; H2O / 1 h
7.1: 0.88 g / N-methylmorpholine oxide; OsO4 / H2O; acetone; tetrahydrofuran / 10 h
With
4-methyl-morpholine; dmap; potassium hydroxide; sodium hydroxide; osmium(VIII) oxide; triflic azide; tetra(n-butyl)ammonium hydrogensulfate; potassium tri-sec-butyl-borohydride; copper(II) sulfate; 4-methylmorpholine N-oxide; isobutyl chloroformate;
In
tetrahydrofuran; ethanol; dichloromethane; water; acetone; benzene;
DOI:10.1021/jo0356863
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 80 percent / tetrahydrofuran / 4 h / -78 °C
2: 14 percent / K-Selectride / tetrahydrofuran / 4 h / -78 °C
3: 75 percent / KOH / H2O; ethanol / 5 h / Heating
4: 85 percent / 4-(dimethylamino)pyridine; CuSO4; triflyl azide / CH2Cl2 / 2 h
5: NaOH; NBu4HSO4 / benzene; H2O / 1 h
6: 0.88 g / N-methylmorpholine oxide; OsO4 / H2O; acetone; tetrahydrofuran / 10 h
With
dmap; potassium hydroxide; sodium hydroxide; osmium(VIII) oxide; triflic azide; tetra(n-butyl)ammonium hydrogensulfate; potassium tri-sec-butyl-borohydride; copper(II) sulfate; 4-methylmorpholine N-oxide;
In
tetrahydrofuran; ethanol; dichloromethane; water; acetone; benzene;
DOI:10.1021/jo0356863
- Guidance literature:
-
Multi-step reaction with 5 steps
1: 14 percent / K-Selectride / tetrahydrofuran / 4 h / -78 °C
2: 75 percent / KOH / H2O; ethanol / 5 h / Heating
3: 85 percent / 4-(dimethylamino)pyridine; CuSO4; triflyl azide / CH2Cl2 / 2 h
4: NaOH; NBu4HSO4 / benzene; H2O / 1 h
5: 0.88 g / N-methylmorpholine oxide; OsO4 / H2O; acetone; tetrahydrofuran / 10 h
With
dmap; potassium hydroxide; sodium hydroxide; osmium(VIII) oxide; triflic azide; tetra(n-butyl)ammonium hydrogensulfate; potassium tri-sec-butyl-borohydride; copper(II) sulfate; 4-methylmorpholine N-oxide;
In
tetrahydrofuran; ethanol; dichloromethane; water; acetone; benzene;
DOI:10.1021/jo0356863
