(3aR,4R,8R,8aR,8bS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-a]pyrrolizin-6-one

Base Information

Chemical Name:(3aR,4R,8R,8aR,8bS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-a]pyrrolizin-6-one
CAS No.:138127-91-0
Molecular Formula:C₂₇H₃₅NO₅Si
Molecular Weight:481.664
Hs Code.:

Synonyms:(3aR,4R,8R,8aR,8bS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-a]pyrrolizin-6-one

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Chemical Property of (3aR,4R,8R,8aR,8bS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-a]pyrrolizin-6-one

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Technology Process of (3aR,4R,8R,8aR,8bS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-a]pyrrolizin-6-one

There total 10 articles about (3aR,4R,8R,8aR,8bS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-a]pyrrolizin-6-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

: 138127-92-1
(R)-3-[(3aS,4R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-3-hydroxy-propionitrile

: 138127-91-0
(3aR,4R,8R,8aR,8bS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-a]pyrrolizin-6-one

Guidance literature:: With ammonium hydroxide; ammonium chloride; In ethanol; at 100 ℃; for 20h;
DOI:10.1016/0040-4039(91)80072-E

Reference yield:

: 127903-44-0
2-azido-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone

: 138127-91-0
(3aR,4R,8R,8aR,8bS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-a]pyrrolizin-6-one

Guidance literature:: Multi-step reaction with 10 steps

1: diisobutylaluminium hydride / tetrahydrofuran

2: NaBH₄ / methanol

3: imidazole / dimethylformamide / 0 °C

4: DMAP / pyridine

5: aq. acetic acid / dioxane

6: Ba(OMe)2 / methanol / 0 °C

7: CH₂Cl₂ / -50 °C

8: CH₂Cl₂; tetrahydrofuran

9: 72 percent / H₂ / Pd/C / ethyl acetate

10: 60 percent / NH₄Cl, 35percent aq. NH₃ / ethanol / 20 h / 100 °C

With 1H-imidazole; dmap; ammonium hydroxide; sodium tetrahydroborate; hydrogen; diisobutylaluminium hydride; barium methoxide; ammonium chloride; acetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(91)80072-E

Reference yield:

: Methanesulfonic acid (S)-{(4R,5R)-5-[(R)-1-azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester

: 138127-91-0
(3aR,4R,8R,8aR,8bS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-a]pyrrolizin-6-one

Guidance literature:: Multi-step reaction with 6 steps

1: aq. acetic acid / dioxane

2: Ba(OMe)2 / methanol / 0 °C

3: CH₂Cl₂ / -50 °C

4: CH₂Cl₂; tetrahydrofuran

5: 72 percent / H₂ / Pd/C / ethyl acetate

6: 60 percent / NH₄Cl, 35percent aq. NH₃ / ethanol / 20 h / 100 °C

With ammonium hydroxide; hydrogen; barium methoxide; ammonium chloride; acetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; ethyl acetate;
DOI:10.1016/0040-4039(91)80072-E