Technology Process of (2S,3R,6R)-6-((S)-1-Benzyloxymethoxy-ethyl)-3,5-dimethyl-3,6-dihydro-2H-pyran-2-carboxylic acid methyl ester
There total 10 articles about (2S,3R,6R)-6-((S)-1-Benzyloxymethoxy-ethyl)-3,5-dimethyl-3,6-dihydro-2H-pyran-2-carboxylic acid methyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 11 steps
1: i-Bu2AlH / diethyl ether / 1 h / -78 °C
2: tetrahydrofuran / 1.) -78 deg C, 2.) 25 deg C, 3 h
3: 93 percent / DMSO, (COCl)2, Et3N / 1.) -60 deg C, 2.) 25 deg C
4: 89 percent / Zn(BH4)2 / diethyl ether / 0.67 h / -78 °C
5: 95 percent / NaH / tetrahydrofuran / 15 h / Heating
6: 80 percent / DMAP, DCC / CH2Cl2 / 1.) 0 deg C, 2.) 25 deg C, 2 h
7: 1.) O3, 2.) Me2S / 1.) CH2Cl2/MeOH, -78 deg C, 2.) -78 deg C, then warming up to 25 deg C
8: diethyl ether; benzene / -78 °C
9: CF3CO2H / benzene / 7 h / Heating
11: diethyl ether
With
dmap; zinc(II) tetrahydroborate; oxalyl dichloride; dimethylsulfide; sodium hydride; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid;
In
tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1016/S0040-4039(00)85502-1
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 89 percent / Zn(BH4)2 / diethyl ether / 0.67 h / -78 °C
2: 95 percent / NaH / tetrahydrofuran / 15 h / Heating
3: 80 percent / DMAP, DCC / CH2Cl2 / 1.) 0 deg C, 2.) 25 deg C, 2 h
4: 1.) O3, 2.) Me2S / 1.) CH2Cl2/MeOH, -78 deg C, 2.) -78 deg C, then warming up to 25 deg C
5: diethyl ether; benzene / -78 °C
6: CF3CO2H / benzene / 7 h / Heating
8: diethyl ether
With
dmap; zinc(II) tetrahydroborate; dimethylsulfide; sodium hydride; ozone; dicyclohexyl-carbodiimide; trifluoroacetic acid;
In
tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1016/S0040-4039(00)85502-1
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 80 percent / DMAP, DCC / CH2Cl2 / 1.) 0 deg C, 2.) 25 deg C, 2 h
2: 1.) O3, 2.) Me2S / 1.) CH2Cl2/MeOH, -78 deg C, 2.) -78 deg C, then warming up to 25 deg C
3: diethyl ether; benzene / -78 °C
4: CF3CO2H / benzene / 7 h / Heating
6: diethyl ether
With
dmap; dimethylsulfide; ozone; dicyclohexyl-carbodiimide; trifluoroacetic acid;
In
diethyl ether; dichloromethane; benzene;
DOI:10.1016/S0040-4039(00)85502-1
