Technology Process of (2S,3R,4S,5S)-2-[4-chloro-3-(4-hydroxy-benzyl)-phenyl]-6,6-bis-hydroxymethyl-2-methoxy-tetrahydro-pyran-3,4,5-triol
There total 5 articles about (2S,3R,4S,5S)-2-[4-chloro-3-(4-hydroxy-benzyl)-phenyl]-6,6-bis-hydroxymethyl-2-methoxy-tetrahydro-pyran-3,4,5-triol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
methyl 1-C-[4-chloro-3-(4-{[(2, 6-dichlorophenyl)sulfonyl]oxy}benzyl)phenyl]-6-O-[(2,6-dichlorophenyl)sulfonyl]-alpha-D-glucopyranoside;
With
2,4,6-trimethyl-pyridine;
In
dimethyl sulfoxide;
at 127 ℃;
formaldehyd;
With
sodium ethanolate;
In
ethanol;
at 55 ℃;
for 16h;
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: boron trichloride / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
1.2: 0 °C
2.1: dmap; 1H-imidazole / N,N-dimethyl-formamide / 0 °C
3.1: n-butyllithium / toluene; hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.2: 1.5 h / -78 °C
3.3: 40 h / -78 - 20 °C
4.1: triethylamine; zinc dibromide / 2-methyltetrahydrofuran / 0 - 20 °C
5.1: 2,4,6-trimethyl-pyridine / dimethyl sulfoxide / 127 °C
5.2: 16 h / 55 °C
With
1H-imidazole; 2,4,6-trimethyl-pyridine; dmap; n-butyllithium; boron trichloride; triethylamine; zinc dibromide;
In
tetrahydrofuran; 2-methyltetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: n-butyllithium / toluene; hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 1.5 h / -78 °C
1.3: 40 h / -78 - 20 °C
2.1: triethylamine; zinc dibromide / 2-methyltetrahydrofuran / 0 - 20 °C
3.1: 2,4,6-trimethyl-pyridine / dimethyl sulfoxide / 127 °C
3.2: 16 h / 55 °C
With
2,4,6-trimethyl-pyridine; n-butyllithium; triethylamine; zinc dibromide;
In
tetrahydrofuran; 2-methyltetrahydrofuran; hexane; dimethyl sulfoxide; toluene;
