Technology Process of (1S,3S,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-ol
There total 12 articles about (1S,3S,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-1-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
L-Selectride;
In
tetrahydrofuran;
at -78 - 22 ℃;
for 3h;
diastereoselective reaction;
DOI:10.1021/jo5005923
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 0.25 h / 18 °C / Inert atmosphere
1.2: 18 h / 0 - 18 °C / Inert atmosphere
2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 4 h / 26 °C
3.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 24 h / 0 - 27 °C
4.1: sodium hydroxide; water / ethanol / 2 h / 110 °C / Microwave irradiation
5.1: triethylamine; methanesulfonyl chloride / dichloromethane / 1.5 h / 0 °C / Inert atmosphere
6.1: triethylamine; oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C
7.1: L-Selectride / tetrahydrofuran / 3 h / -78 - 22 °C
With
oxalyl dichloride; di-isopropyl azodicarboxylate; water; tetra-(n-butyl)ammonium iodide; L-Selectride; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide;
In
tetrahydrofuran; ethanol; dichloromethane; water; toluene;
3.1: |Mitsunobu Displacement / 6.1: |Swern Oxidation;
DOI:10.1021/jo5005923
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 4 h / 26 °C
2: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 24 h / 0 - 27 °C
3: sodium hydroxide; water / ethanol / 2 h / 110 °C / Microwave irradiation
4: triethylamine; methanesulfonyl chloride / dichloromethane / 1.5 h / 0 °C / Inert atmosphere
5: triethylamine; oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C
6: L-Selectride / tetrahydrofuran / 3 h / -78 - 22 °C
With
oxalyl dichloride; di-isopropyl azodicarboxylate; water; L-Selectride; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide;
In
tetrahydrofuran; ethanol; dichloromethane; water; toluene;
2: |Mitsunobu Displacement / 5: |Swern Oxidation;
DOI:10.1021/jo5005923
