((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

Base Information

• Chemical Name: ((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
• CAS No.: 138040-29-6
• Molecular Formula: C₂₇H₃₄N₄O₄Si
• Molecular Weight: 506.677
• Mol file: 138040-29-6.mol

Synonyms:((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

Chemical Property of ((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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((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

There total 8 articles about ((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 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:

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

Guidance literature:

Multi-step reaction with 8 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

With 1H-imidazole; dmap; sodium tetrahydroborate; diisobutylaluminium hydride; barium methoxide; acetic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; 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 → ((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)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. acetic acid / dioxane

2: Ba(OMe)2 / methanol / 0 °C

3: CH₂Cl₂ / -50 °C

4: CH₂Cl₂; tetrahydrofuran

With barium methoxide; acetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

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-heptose → ((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)

Guidance literature:

Multi-step reaction with 7 steps

1: NaBH₄ / methanol

2: imidazole / dimethylformamide / 0 °C

3: DMAP / pyridine

4: aq. acetic acid / dioxane

5: Ba(OMe)2 / methanol / 0 °C

6: CH₂Cl₂ / -50 °C

7: CH₂Cl₂; tetrahydrofuran

With 1H-imidazole; dmap; sodium tetrahydroborate; barium methoxide; acetic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;

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

upstream raw materials:

lithium cyanide

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

Downstream raw materials:

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

(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