Technology Process of methyl (2Z)-3-[(4R,5S,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]acrylate
There total 12 articles about methyl (2Z)-3-[(4R,5S,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]acrylate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
18-crown-6 ether; potassium hexamethylsilazane;
In
tetrahydrofuran; toluene;
at -78 ℃;
for 0.5h;
DOI:10.1021/jo0356356
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: (Cyclohexyl)2BCl; Et3N / diethyl ether / 1 h / 0 °C
1.2: diethyl ether / 5 h / -78 °C
2.1: tetramethylammonium triacetoxyborohydride; AcOH / acetonitrile / 18 h / -30 °C
3.1: 80 percent / CSA; 3 Angstroem molecular sieves / acetone / 12 h / 20 °C
4.1: 72 percent / HF; pyridine / tetrahydrofuran / 20 °C
5.1: 82 percent / K2CO3 / methanol / 1 h / 20 °C
6.1: 95 percent / aq. NaIO4 / tetrahydrofuran / 1 h / 20 °C
7.1: 86 percent / KHMDS; 18-crown-6 / toluene; tetrahydrofuran / 0.5 h / -78 °C
With
pyridine; sodium periodate; 18-crown-6 ether; 3 A molecular sieve; camphor-10-sulfonic acid; dicyclohexylboron chloride; hydrogen fluoride; potassium hexamethylsilazane; potassium carbonate; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; methanol; diethyl ether; acetone; toluene; acetonitrile;
7.1: Still-Gennari olefination;
DOI:10.1021/jo0356356
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 70 percent / imidazole / dimethylformamide / 2 h / 20 °C
2.1: Et3N; DMAP / CH2Cl2 / 2 h / 20 °C
3.1: (Cyclohexyl)2BCl; Et3N / diethyl ether / 1 h / 0 °C
3.2: diethyl ether / 5 h / -78 °C
4.1: tetramethylammonium triacetoxyborohydride; AcOH / acetonitrile / 18 h / -30 °C
5.1: 80 percent / CSA; 3 Angstroem molecular sieves / acetone / 12 h / 20 °C
6.1: 72 percent / HF; pyridine / tetrahydrofuran / 20 °C
7.1: 82 percent / K2CO3 / methanol / 1 h / 20 °C
8.1: 95 percent / aq. NaIO4 / tetrahydrofuran / 1 h / 20 °C
9.1: 86 percent / KHMDS; 18-crown-6 / toluene; tetrahydrofuran / 0.5 h / -78 °C
With
pyridine; 1H-imidazole; dmap; sodium periodate; 18-crown-6 ether; 3 A molecular sieve; camphor-10-sulfonic acid; dicyclohexylboron chloride; hydrogen fluoride; potassium hexamethylsilazane; potassium carbonate; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
9.1: Still-Gennari olefination;
DOI:10.1021/jo0356356
