Technology Process of (S)-2-{(2R,4R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-propionaldehyde
There total 15 articles about (S)-2-{(2R,4R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-propionaldehyde which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
oxalyl dichloride; dimethyl sulfoxide; triethylamine;
In
dichloromethane;
at -78 - -20 ℃;
DOI:10.1021/jo020537q
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 92 percent / N-iodosuccinimide / CH2Cl2 / 15 h / -23 - 0 °C
2.1: 97 percent / OsO4; sodium periodate / tetrahydrofuran; H2O; propan-2-ol / 15 h
3.1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / 0.67 h / -78 °C
3.2: 65 percent / tetrahydrofuran; toluene / 0.92 h / -78 °C
4.1: 86 percent / tri-n-butylstannane; azobisisobutyronitrile / toluene / 2 h / 80 °C
5.1: 87 percent / MgBr2*OEt2 / diethyl ether / 2 h / 20 °C
6.1: 92 percent / NaBH4; CaCl2 / ethanol; tetrahydrofuran / 4 h / 0 - 20 °C
7.1: 76 percent / triethylamine; 4-dimethylaminopyridine / CH2Cl2 / 4 h / 20 °C
8.1: 93 percent / acetic acid / tetrahydrofuran; H2O / 18 h / 20 °C
9.1: 71 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - -20 °C
With
dmap; sodium tetrahydroborate; sodium periodate; N-iodo-succinimide; osmium(VIII) oxide; oxalyl dichloride; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; potassium hexamethylsilazane; acetic acid; dimethyl sulfoxide; triethylamine; calcium chloride; magnesium bromide;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; isopropyl alcohol; toluene;
3.2: Wadsworth-Emmons condensation;
DOI:10.1021/jo020537q
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 97 percent / OsO4; sodium periodate / tetrahydrofuran; H2O; propan-2-ol / 15 h
2.1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / 0.67 h / -78 °C
2.2: 65 percent / tetrahydrofuran; toluene / 0.92 h / -78 °C
3.1: 86 percent / tri-n-butylstannane; azobisisobutyronitrile / toluene / 2 h / 80 °C
4.1: 87 percent / MgBr2*OEt2 / diethyl ether / 2 h / 20 °C
5.1: 92 percent / NaBH4; CaCl2 / ethanol; tetrahydrofuran / 4 h / 0 - 20 °C
6.1: 76 percent / triethylamine; 4-dimethylaminopyridine / CH2Cl2 / 4 h / 20 °C
7.1: 93 percent / acetic acid / tetrahydrofuran; H2O / 18 h / 20 °C
8.1: 71 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - -20 °C
With
dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; potassium hexamethylsilazane; acetic acid; dimethyl sulfoxide; triethylamine; calcium chloride; magnesium bromide;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; isopropyl alcohol; toluene;
2.2: Wadsworth-Emmons condensation;
DOI:10.1021/jo020537q
![(R)-2-{(2R,4R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-propan-1-ol](/Databaselist/images/loading.webp)
