Technology Process of (2S,3R)-ethyl 2-azido-3-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxypropanoate
There total 11 articles about (2S,3R)-ethyl 2-azido-3-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxypropanoate which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
C23H26O8S;
With
sodium azide;
In
N,N-dimethyl-formamide;
at 80 ℃;
for 2h;
Inert atmosphere;
With
water;
In
N,N-dimethyl-formamide;
at 20 ℃;
stereoselective reaction;
Inert atmosphere;
Cooling with ice;
DOI:10.1016/j.tetlet.2011.09.043
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.33 h / 0 - 20 °C / Inert atmosphere
1.2: 2 h / 0 - 20 °C / Inert atmosphere
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.67 h / -78 °C / Inert atmosphere
2.2: -78 - 0 °C / Inert atmosphere
3.1: toluene / 6 h / Inert atmosphere; Reflux
4.1: osmium(VIII) oxide; water; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III) / tert-butyl alcohol / 24.08 h / 0 °C / Inert atmosphere
5.1: thionyl chloride; triethylamine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
6.1: sodium azide / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere
6.2: 20 °C / Inert atmosphere; Cooling with ice
With
osmium(VIII) oxide; lithium aluminium tetrahydride; thionyl chloride; sodium azide; oxalyl dichloride; water; potassium carbonate; dimethyl sulfoxide; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; potassium hexacyanoferrate(III);
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Wittig reaction;
DOI:10.1016/j.tetlet.2011.09.043
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: toluene / 4 h / Inert atmosphere; Reflux
2.1: AD-mix-α; methanesulfonamide; water / tert-butyl alcohol / 24 h / 0 °C / Inert atmosphere
3.1: toluene-4-sulfonic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.33 h / 0 - 20 °C / Inert atmosphere
4.2: 2 h / 0 - 20 °C / Inert atmosphere
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.67 h / -78 °C / Inert atmosphere
5.2: -78 - 0 °C / Inert atmosphere
6.1: toluene / 6 h / Inert atmosphere; Reflux
7.1: osmium(VIII) oxide; water; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III) / tert-butyl alcohol / 24.08 h / 0 °C / Inert atmosphere
8.1: thionyl chloride; triethylamine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
9.1: sodium azide / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere
9.2: 20 °C / Inert atmosphere; Cooling with ice
With
osmium(VIII) oxide; lithium aluminium tetrahydride; thionyl chloride; sodium azide; oxalyl dichloride; methanesulfonamide; AD-mix-α; water; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; potassium hexacyanoferrate(III);
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
1.1: Wittig reaction / 2.1: Sharpless dihydroxylation / 5.1: Swern oxidation / 5.2: Swern oxidation / 6.1: Wittig reaction;
DOI:10.1016/j.tetlet.2011.09.043
