Technology Process of (2S,2'S,5'R)-5'-((E)-(S)-8-Benzyloxy-1-hydroxy-oct-4-enyl)-tetrahydro-[2,2']bifuranyl-5-one
There total 11 articles about (2S,2'S,5'R)-5'-((E)-(S)-8-Benzyloxy-1-hydroxy-oct-4-enyl)-tetrahydro-[2,2']bifuranyl-5-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
camphor-10-sulfonic acid;
In
methanol; dichloromethane;
at 0 ℃;
DOI:10.1021/jo050697c
- 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: oxone; K2CO3; Na2B4O7*10H2O / L-fructose-based (+)-Shi catalyst; nBu4NHSO4 / H2O; various solvent(s); acetonitrile / 2.5 h / 0 °C
8.1: camphorsulfonic acid / CH2Cl2; methanol / 0 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; borax; Oxone; sodium hydroxide; n-butyllithium; diethyl (2R,3R)-tartrate; di-isopropyl azodicarboxylate; camphor-10-sulfonic acid; potassium carbonate; toluene-4-sulfonic acid; diisopropylamine; triphenylphosphine;
L-fructose-based (+)-Shi catalyst; tetra(n-butyl)ammonium hydrogensulfate;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetonitrile;
2.1: Sharpless asymmetric epoxidation / 4.1: Mitsunobu reaction / 7.1: Shi asymmetric epoxidation;
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: oxone; K2CO3; Na2B4O7*10H2O / L-fructose-based (+)-Shi catalyst; nBu4NHSO4 / H2O; various solvent(s); acetonitrile / 2.5 h / 0 °C
9.1: camphorsulfonic acid / CH2Cl2; methanol / 0 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; borax; Oxone; sodium hydroxide; n-butyllithium; oxalyl dichloride; diethyl (2R,3R)-tartrate; di-isopropyl azodicarboxylate; camphor-10-sulfonic acid; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; diisopropylamine; triphenylphosphine;
L-fructose-based (+)-Shi catalyst; tetra(n-butyl)ammonium hydrogensulfate;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetonitrile;
1.1: Swern oxidation / 3.1: Sharpless asymmetric epoxidation / 5.1: Mitsunobu reaction / 8.1: Shi asymmetric epoxidation;
DOI:10.1021/jo050697c
![(S)-5-{(S)-3-[(2S,3S)-3-((E)-7-Benzyloxy-hept-3-enyl)-oxiranyl]-1-hydroxy-propyl}-dihydro-furan-2-one](/Databaselist/images/loading.webp)
