Technology Process of Methanesulfonic acid (E)-(S)-8-benzyloxy-1-((2S,5S,2'S)-5'-oxo-octahydro-[2,2']bifuranyl-5-yl)-oct-4-enyl ester
There total 11 articles about Methanesulfonic acid (E)-(S)-8-benzyloxy-1-((2S,5S,2'S)-5'-oxo-octahydro-[2,2']bifuranyl-5-yl)-oct-4-enyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 60 percent / diethyl ether; tetrahydrofuran / 1 h / -78 °C
2.1: L-(+)-diethyl tartrate; Ti(O-iPr)4; tert-BuOOH / CH2Cl2; hexane / 48 h / -20 °C
3.1: n-BuLi; iPr2NH / tetrahydrofuran; hexane / 0.42 h
3.2: tetrahydrofuran; hexane / 3 h / Heating
3.3: PTSA*H2O / benzene / 1 h / Heating
4.1: diisopropyl azodicarboxylate; PPh3 / tetrahydrofuran / 12 h / 20 °C
5.1: aqueous NaOH / methanol / 2 h / 60 °C
6.1: PTSA*H2O / CH2Cl2 / 1 h / 20 °C
7.1: TFAA; Re2O7; 2,6-lutidine / CH2Cl2 / 6 h / 0 - 20 °C
8.1: triethylamine
With
2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; diethyl (2R,3R)-tartrate; di-isopropyl azodicarboxylate; toluene-4-sulfonic acid; rhenium(VII) oxide; triethylamine; diisopropylamine; triphenylphosphine; trifluoroacetic anhydride;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;
2.1: Sharpless asymmetric epoxidation / 4.1: Mitsunobu reaction;
DOI:10.1021/jo050697c
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 91 percent / DMSO; oxalyl chloride; Et3N / CH2Cl2 / 1.5 h / -78 - 0 °C
2.1: 60 percent / diethyl ether; tetrahydrofuran / 1 h / -78 °C
3.1: L-(+)-diethyl tartrate; Ti(O-iPr)4; tert-BuOOH / CH2Cl2; hexane / 48 h / -20 °C
4.1: n-BuLi; iPr2NH / tetrahydrofuran; hexane / 0.42 h
4.2: tetrahydrofuran; hexane / 3 h / Heating
4.3: PTSA*H2O / benzene / 1 h / Heating
5.1: diisopropyl azodicarboxylate; PPh3 / tetrahydrofuran / 12 h / 20 °C
6.1: aqueous NaOH / methanol / 2 h / 60 °C
7.1: PTSA*H2O / CH2Cl2 / 1 h / 20 °C
8.1: TFAA; Re2O7; 2,6-lutidine / CH2Cl2 / 6 h / 0 - 20 °C
9.1: triethylamine
With
2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; oxalyl dichloride; diethyl (2R,3R)-tartrate; di-isopropyl azodicarboxylate; toluene-4-sulfonic acid; rhenium(VII) oxide; dimethyl sulfoxide; triethylamine; diisopropylamine; triphenylphosphine; trifluoroacetic anhydride;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;
1.1: Swern oxidation / 3.1: Sharpless asymmetric epoxidation / 5.1: Mitsunobu reaction;
DOI:10.1021/jo050697c
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: L-(+)-diethyl tartrate; Ti(O-iPr)4; tert-BuOOH / CH2Cl2; hexane / 48 h / -20 °C
2.1: n-BuLi; iPr2NH / tetrahydrofuran; hexane / 0.42 h
2.2: tetrahydrofuran; hexane / 3 h / Heating
2.3: PTSA*H2O / benzene / 1 h / Heating
3.1: diisopropyl azodicarboxylate; PPh3 / tetrahydrofuran / 12 h / 20 °C
4.1: aqueous NaOH / methanol / 2 h / 60 °C
5.1: PTSA*H2O / CH2Cl2 / 1 h / 20 °C
6.1: TFAA; Re2O7; 2,6-lutidine / CH2Cl2 / 6 h / 0 - 20 °C
7.1: triethylamine
With
2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; diethyl (2R,3R)-tartrate; di-isopropyl azodicarboxylate; toluene-4-sulfonic acid; rhenium(VII) oxide; triethylamine; diisopropylamine; triphenylphosphine; trifluoroacetic anhydride;
In
tetrahydrofuran; methanol; hexane; dichloromethane;
1.1: Sharpless asymmetric epoxidation / 3.1: Mitsunobu reaction;
DOI:10.1021/jo050697c
