Technology Process of (4R,6S)-4-benzyloxymethyl-2,2,6-trimethyl-[1,3]dioxane-4-carbonitrile
There total 1 articles about (4R,6S)-4-benzyloxymethyl-2,2,6-trimethyl-[1,3]dioxane-4-carbonitrile which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(6S)-2,2,6-trimethyl-[1,3]dioxane-4-carbonitrile;
With
n-butyllithium; diethylamine;
In
tetrahydrofuran; hexane;
at -78 ℃;
for 2.5h;
Benzyloxymethyl chloride;
In
tetrahydrofuran;
at -78 ℃;
for 5.16667h;
With
diethylamine;
In
tetrahydrofuran;
at -78 - 23 ℃;
for 10h;
DOI:10.1021/ol0480832
- Guidance literature:
-
With
ruthenium trichloride; sodium periodate; disodium hydrogenphosphate;
In
tetrachloromethane; water; acetonitrile;
at 23 ℃;
for 9h;
DOI:10.1021/ol0480832
-
![(2S,3aS,4R,5R,7aS)-2-allyl-3-ethoxy-7a-(hydroxymethyl)-2-phenyl-4-vinyl-3-a,6,7,7a-tetrahydro-4H,4H-spiro[1,3-benzodioxole-5,1-cyclohexa[2,5]dien]-4-one](/Databaselist/images/loading.webp)
-
(2S,3aS,4R,5R,7aS)-2-allyl-3-ethoxy-7a-(hydroxymethyl)-2-phenyl-4-vinyl-3-a,6,7,7a-tetrahydro-4H,4H-spiro[1,3-benzodioxole-5,1-cyclohexa[2,5]dien]-4-one
- Guidance literature:
-
Multi-step reaction with 12 steps
1: 71 percent / Na2HPO4*12H2O; NaIO4; RuCl3*xH2O / CCl4; acetonitrile; H2O / 9 h / 23 °C
2: DIBAL-H / diethyl ether / 1 h / -78 °C
3: imidazole; DMAP / dimethylformamide / 0 - 23 °C
4: 94 percent / DIBAL-H; n-BuLi / diethyl ether; hexane / 0.47 h / 0 °C
5: activated Zn / dimethylformamide / 0 - 23 °C
6: 41 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C
7: 66 percent / CSA / toluene / 0.33 h / 25 °C / 22.5 Torr
8: 78 percent / 4-toluenesulfonic acid hydrate / methanol / 2.5 h / 25 °C
9: 82 percent / LDA / tetrahydrofuran / -78 - 0 °C
10: 90 percent / K2CO3 / acetone / 6 h / Heating
11: DMAP / CH2Cl2 / 2 h / 23 °C
12: K2CO3 / methanol / 23 °C
With
1H-imidazole; dmap; ruthenium trichloride; sodium periodate; disodium hydrogenphosphate; n-butyllithium; camphor-10-sulfonic acid; p-toluenesulfonic acid monohydrate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; zinc; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1021/ol0480832
