(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

Base Information

• Chemical Name: (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
• CAS No.: 138127-92-1
• Molecular Formula: C₂₇H₃₆N₂O₄Si
• Molecular Weight: 480.679
• Mol file: 138127-92-1.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 9 articles about (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 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: 72.0%

((2R,3R)-3-{(4R,5R)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-oxiranyl)-acetonitrile (138040-29-6) → (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 (138127-92-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1016/0040-4039(91)80072-E

Reference yield:

2-azido-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone (127903-44-0) → (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 (138127-92-1)

Guidance literature:

Multi-step reaction with 9 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

With 1H-imidazole; dmap; sodium tetrahydroborate; hydrogen; diisobutylaluminium hydride; barium methoxide; acetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; 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 → (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 (138127-92-1)

Guidance literature:

Multi-step reaction with 5 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

With hydrogen; barium methoxide; acetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethyl acetate;

DOI:10.1016/0040-4039(91)80072-E

upstream raw materials:

((2R,3R)-3-{(4R,5R)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-oxiranyl)-acetonitrile

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

Downstream raw materials:

(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

(3aR,4R,8aS,8bS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-a]pyrrolizine-6,8-dione

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