Technology Process of (4S,6R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-4-hydroxy-tetrahydro-pyran-2-one
There total 10 articles about (4S,6R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-4-hydroxy-tetrahydro-pyran-2-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-5,6-dihydro-pyran-2-one;
With
sodium hydroxide; dihydrogen peroxide;
In
methanol;
for 1.5h;
With
sodium tetrahydroborate; diphenyl diselenide; acetic acid;
In
isopropyl alcohol;
at 0 ℃;
for 0.5h;
DOI:10.1016/j.tetlet.2003.08.023
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 80 percent / TiCl4; Et3N / CH2Cl2 / 1.5 h / 0 °C
2.1: 94 percent / LiBH4 / methanol; tetrahydrofuran / 1 h / 23 °C
3.1: (COCl)2; DMSO; Et3N / CH2Cl2 / 0.75 h / -60 °C
4.1: NaH / tetrahydrofuran / 2 h / -78 - -20 °C
5.1: 96 percent / Dibal-H / CH2Cl2 / 1 h / -78 - -40 °C
6.1: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 1.5 h / 23 °C
7.1: diethyl ether / 3 h / -80 °C
8.1: 77 percent / Et3N / CH2Cl2 / 2 h / 0 °C
9.1: 83 percent / Cl2(Pcy)2Ru=CHPh / CH2Cl2 / 12 h / 40 °C
10.1: H2O2; aq. NaOH / methanol / 1.5 h
10.2: 74 percent / NaBH4; PhSeSePh; AcOH / propan-2-ol / 0.5 h / 0 °C
With
sodium hydroxide; lithium borohydride; oxalyl dichloride; dihydrogen peroxide; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine;
Grubbs catalyst first generation;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane;
3.1: Swern oxidation / 4.1: Horner-Emmons reaction;
DOI:10.1016/j.tetlet.2003.08.023
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: NaH / tetrahydrofuran / 2 h / -78 - -20 °C
2.1: 96 percent / Dibal-H / CH2Cl2 / 1 h / -78 - -40 °C
3.1: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 1.5 h / 23 °C
4.1: diethyl ether / 3 h / -80 °C
5.1: 77 percent / Et3N / CH2Cl2 / 2 h / 0 °C
6.1: 83 percent / Cl2(Pcy)2Ru=CHPh / CH2Cl2 / 12 h / 40 °C
7.1: H2O2; aq. NaOH / methanol / 1.5 h
7.2: 74 percent / NaBH4; PhSeSePh; AcOH / propan-2-ol / 0.5 h / 0 °C
With
sodium hydroxide; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine;
Grubbs catalyst first generation;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane;
1.1: Horner-Emmons reaction;
DOI:10.1016/j.tetlet.2003.08.023
