Technology Process of (1S,1'S,2S,3R)-2-{1-hydroxy-2'-[4-(methoxyphenyl)methoxy]oxy}methyl-3-(methoxymethoxy)oxy-1-phenylsulfonyl-1-vinylcyclopentane
There total 10 articles about (1S,1'S,2S,3R)-2-{1-hydroxy-2'-[4-(methoxyphenyl)methoxy]oxy}methyl-3-(methoxymethoxy)oxy-1-phenylsulfonyl-1-vinylcyclopentane which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
2.1: tBuOK / tetrahydrofuran / 0.5 h / -42 °C
3.1: 12.7 g / DIBAL-H / toluene; hexane / 0.5 h / -78 °C
4.1: 89 percent / Ti(OPr-i)4; D-(-)-diethyl tartrate; TBHP / CH2Cl2 / 5 h / -20 °C
5.1: 95 percent / NaH / tetrahydrofuran; dimethylformamide / 1 h / 0 °C
6.1: TBAF / tetrahydrofuran / 1 h / 20 °C
7.1: 3.89 g / DMAP / CH2Cl2 / 0.25 h / 0 °C
8.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
8.2: 99 percent / tetrahydrofuran / -78 - 20 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; n-butyllithium; oxalyl dichloride; diethyl (2S,3S)-tartrate; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
1.1: Oxidation / 2.1: Horner-Emmons reaction / 3.1: Reduction / 4.1: Epoxidation / 5.1: Alkylation / 6.1: desilylation / 7.1: mesylation / 8.1: Metallation / 8.2: Cyclization;
DOI:10.1016/S0040-4020(00)00730-4
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: LiAlH4 / diethyl ether / 0.17 h / 0 °C
2.1: imidazole / dimethylformamide / 3 h / 20 °C
3.1: 75.0 g / liquid NH3 / tetrahydrofuran; ethanol / 0.5 h / -34 °C
4.1: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
5.1: tBuOK / tetrahydrofuran / 0.5 h / -42 °C
6.1: 12.7 g / DIBAL-H / toluene; hexane / 0.5 h / -78 °C
7.1: 89 percent / Ti(OPr-i)4; D-(-)-diethyl tartrate; TBHP / CH2Cl2 / 5 h / -20 °C
8.1: 95 percent / NaH / tetrahydrofuran; dimethylformamide / 1 h / 0 °C
9.1: TBAF / tetrahydrofuran / 1 h / 20 °C
10.1: 3.89 g / DMAP / CH2Cl2 / 0.25 h / 0 °C
11.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
11.2: 99 percent / tetrahydrofuran / -78 - 20 °C
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; diethyl (2S,3S)-tartrate; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
1.1: Reduction / 2.1: Substitution / 3.1: detritylation / 4.1: Oxidation / 5.1: Horner-Emmons reaction / 6.1: Reduction / 7.1: Epoxidation / 8.1: Alkylation / 9.1: desilylation / 10.1: mesylation / 11.1: Metallation / 11.2: Cyclization;
DOI:10.1016/S0040-4020(00)00730-4
