Technology Process of 4-[(4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-butan-2-one
There total 10 articles about 4-[(4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-butan-2-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
2-diethylaminopropionitrile; tert-Butyl-[(4aR,6S,7R,8aS)-6-(2-iodo-ethyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-dimethyl-silane;
With
lithium diisopropyl amide;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;
at -78 ℃;
With
water; silica gel;
Further stages.;
DOI:10.1021/ol026804w
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 90 percent / aq. HCl / CHCl3 / 20 °C
2.1: CSA / CH2Cl2 / 20 °C
3.1: N-methylmorpholine / CH2Cl2 / 20 °C
4.1: 98 percent / MeI; NaHCO3 / H2O; acetonitrile / 20 °C
5.1: 95 percent / SmI2 / methanol; tetrahydrofuran / 0 °C
6.1: 2,6-lutidine / CH2Cl2 / 0 °C
7.1: DIBAH / CH2Cl2 / 0 °C
8.1: 2,6-lutidine / CH2Cl2 / -78 °C
9.1: NaI / acetone / 60 °C
10.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C
10.2: 100 percent / SiO2; H2O
With
4-methyl-morpholine; 2,6-dimethylpyridine; hydrogenchloride; samarium diiodide; camphor-10-sulfonic acid; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium iodide; lithium diisopropyl amide; methyl iodide;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; chloroform; water; acetone; acetonitrile;
3.1: hetero-Michael reaction;
DOI:10.1021/ol026804w
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: CSA / CH2Cl2 / 20 °C
2.1: N-methylmorpholine / CH2Cl2 / 20 °C
3.1: 98 percent / MeI; NaHCO3 / H2O; acetonitrile / 20 °C
4.1: 95 percent / SmI2 / methanol; tetrahydrofuran / 0 °C
5.1: 2,6-lutidine / CH2Cl2 / 0 °C
6.1: DIBAH / CH2Cl2 / 0 °C
7.1: 2,6-lutidine / CH2Cl2 / -78 °C
8.1: NaI / acetone / 60 °C
9.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C
9.2: 100 percent / SiO2; H2O
With
4-methyl-morpholine; 2,6-dimethylpyridine; samarium diiodide; camphor-10-sulfonic acid; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium iodide; lithium diisopropyl amide; methyl iodide;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; acetone; acetonitrile;
2.1: hetero-Michael reaction;
DOI:10.1021/ol026804w
