(S)-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

Base Information

Chemical Name:(S)-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
CAS No.:138040-18-3
Molecular Formula:C₂₇H₃₆N₂O₄Si
Molecular Weight:480.679
Hs Code.:

(S)-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

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Chemical Property of (S)-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

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Technology Process of (S)-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

There total 13 articles about (S)-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 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:

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

: 138040-18-3
(S)-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

Guidance literature:: Multi-step reaction with 2 steps

1: CH₂Cl₂; tetrahydrofuran

2: 1) H₂ / 1) Pd/C / 1) EtOAc, 2) spontaneous cyclization

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;
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}-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester

: 138040-18-3
(S)-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

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / aq. acetic acid / dioxane

2: 89 percent / Ba(OMe)2 / methanol

3: pyridine / CH₂Cl₂ / -50 °C

4: CH₂Cl₂; tetrahydrofuran

5: 1) H₂ / 1) Pd/C / 1) EtOAc, 2) spontaneous cyclization

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

Reference yield:

: (3aR,4R,7S,7aR)-7-Azido-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ol

: 138040-18-3
(S)-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

Guidance literature:: Multi-step reaction with 8 steps

1: 89 percent / NaBH₄ / ethanol

2: 79 percent / imidazole / dimethylformamide / 0 °C

3: 83 percent / DMAP / pyridine

4: 92 percent / aq. acetic acid / dioxane

5: 89 percent / Ba(OMe)2 / methanol

6: pyridine / CH₂Cl₂ / -50 °C

7: CH₂Cl₂; tetrahydrofuran

8: 1) H₂ / 1) Pd/C / 1) EtOAc, 2) spontaneous cyclization

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