Technology Process of (2S,3R,6R)-6-Benzyloxymethyl-2-bromoethynyl-2-methyl-tetrahydro-pyran-3-ol
There total 12 articles about (2S,3R,6R)-6-Benzyloxymethyl-2-bromoethynyl-2-methyl-tetrahydro-pyran-3-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
boron trifluoride diethyl etherate;
In
dichloromethane;
at -78 - -10 ℃;
DOI:10.1021/ja000001r
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 63 percent / TfOH / CH2Cl2; pentane / 30 h / 0 °C
2.1: DIBAL / toluene / 1 h / -78 °C
3.1: 2.04 g / benzene / 2 h / Heating
4.1: 95 percent / imidazole / dimethylformamide / 3 h / 20 °C
5.1: 72 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C
6.1: 86 percent / (-)-D-diethyl tartrate; Ti(O-i-Pr)4; tert-butylhydroperoxide / CH2Cl2; decane / 5 h / -23 °C
7.1: 92 percent / Et3N; SO3*pyridine / CH2Cl2; dimethylsulfoxide / 4 h / 0 °C
8.1: PPh3 / CH2Cl2 / 0.33 h / 0 °C
8.2: 91 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
9.1: 88 percent / TBAF / tetrahydrofuran / 9 h / 20 °C
10.1: 91 percent / BF3*OEt2 / CH2Cl2 / 6.5 h / -78 - -10 °C
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO3 complex; diethyl (2S,3S)-tartrate; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; triphenylphosphine;
In
tetrahydrofuran; decane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; pentane; benzene;
6.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol990648k
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 63 percent / TfOH / CH2Cl2; pentane / 30 h / 0 °C
2.1: DIBAL / toluene / 1 h / -78 °C
3.1: 2.04 g / benzene / 2 h / Heating
4.1: 95 percent / imidazole / dimethylformamide / 3 h / 20 °C
5.1: 72 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C
6.1: 86 percent / (-)-D-diethyl tartrate; Ti(O-i-Pr)4; tert-butylhydroperoxide / CH2Cl2; decane / 5 h / -23 °C
7.1: 92 percent / Et3N; SO3*pyridine / CH2Cl2; dimethylsulfoxide / 4 h / 0 °C
8.1: PPh3 / CH2Cl2 / 0.33 h / 0 °C
8.2: 91 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
9.1: 88 percent / TBAF / tetrahydrofuran / 9 h / 20 °C
10.1: 91 percent / BF3*OEt2 / CH2Cl2 / 6.5 h / -78 - -10 °C
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO3 complex; diethyl (2S,3S)-tartrate; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; triphenylphosphine;
In
tetrahydrofuran; decane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; pentane; benzene;
6.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol990648k
