Technology Process of (2S,2'S,5'S,2''R,5''S)-5''-((S)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one
There total 13 articles about (2S,2'S,5'S,2''R,5''S)-5''-((S)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one 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:
-
Multi-step reaction with 10 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
9.1: K3Fe(CN)6; K2CO3; MeSO2NH2 / K2OsO2(OH)4; (DHQ)PHAL / H2O; 2-methyl-propan-2-ol / 0 °C
10.1: pyridine / 2 h / 140 °C
With
pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; diethyl (2R,3R)-tartrate; methanesulfonamide; di-isopropyl azodicarboxylate; potassium carbonate; toluene-4-sulfonic acid; rhenium(VII) oxide; triethylamine; diisopropylamine; triphenylphosphine; trifluoroacetic anhydride; potassium hexacyanoferrate(III);
potassium dioxotetrahydroxoosmate(VI); 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol;
2.1: Sharpless asymmetric epoxidation / 4.1: Mitsunobu reaction / 9.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo050697c
- Guidance literature:
-
Multi-step reaction with 11 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
10.1: K3Fe(CN)6; K2CO3; MeSO2NH2 / K2OsO2(OH)4; (DHQ)PHAL / H2O; 2-methyl-propan-2-ol / 0 °C
11.1: pyridine / 2 h / 140 °C
With
pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; oxalyl dichloride; diethyl (2R,3R)-tartrate; methanesulfonamide; di-isopropyl azodicarboxylate; potassium carbonate; toluene-4-sulfonic acid; rhenium(VII) oxide; dimethyl sulfoxide; triethylamine; diisopropylamine; triphenylphosphine; trifluoroacetic anhydride; potassium hexacyanoferrate(III);
potassium dioxotetrahydroxoosmate(VI); 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol;
1.1: Swern oxidation / 3.1: Sharpless asymmetric epoxidation / 5.1: Mitsunobu reaction / 10.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo050697c
- Guidance literature:
-
Multi-step reaction with 9 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
8.1: K3Fe(CN)6; K2CO3; MeSO2NH2 / K2OsO2(OH)4; (DHQ)PHAL / H2O; 2-methyl-propan-2-ol / 0 °C
9.1: pyridine / 2 h / 140 °C
With
pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; diethyl (2R,3R)-tartrate; methanesulfonamide; di-isopropyl azodicarboxylate; potassium carbonate; toluene-4-sulfonic acid; rhenium(VII) oxide; triethylamine; diisopropylamine; triphenylphosphine; trifluoroacetic anhydride; potassium hexacyanoferrate(III);
potassium dioxotetrahydroxoosmate(VI); 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; tert-butyl alcohol;
1.1: Sharpless asymmetric epoxidation / 3.1: Mitsunobu reaction / 8.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo050697c
