(2S,3R)-3-[(R)-4-Azido-3-(tert-butyl-dimethyl-silanyloxy)-butyrylamino]-3-{(4S,5S)-5-[(2E,4E)-5-(4-ethoxy-phenyl)-penta-2,4-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

Base Information

• Chemical Name: (2S,3R)-3-[(R)-4-Azido-3-(tert-butyl-dimethyl-silanyloxy)-butyrylamino]-3-{(4S,5S)-5-[(2E,4E)-5-(4-ethoxy-phenyl)-penta-2,4-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester
• CAS No.: 645394-72-5
• Molecular Formula: C₃₇H₅₅N₅O₁₁Si
• Molecular Weight: 773.956

Synonyms:(2S,3R)-3-[(R)-4-Azido-3-(tert-butyl-dimethyl-silanyloxy)-butyrylamino]-3-{(4S,5S)-5-[(2E,4E)-5-(4-ethoxy-phenyl)-penta-2,4-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

Chemical Property of (2S,3R)-3-[(R)-4-Azido-3-(tert-butyl-dimethyl-silanyloxy)-butyrylamino]-3-{(4S,5S)-5-[(2E,4E)-5-(4-ethoxy-phenyl)-penta-2,4-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (2S,3R)-3-[(R)-4-Azido-3-(tert-butyl-dimethyl-silanyloxy)-butyrylamino]-3-{(4S,5S)-5-[(2E,4E)-5-(4-ethoxy-phenyl)-penta-2,4-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

There total 25 articles about (2S,3R)-3-[(R)-4-Azido-3-(tert-butyl-dimethyl-silanyloxy)-butyrylamino]-3-{(4S,5S)-5-[(2E,4E)-5-(4-ethoxy-phenyl)-penta-2,4-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester 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:

1,2-anhydro-3,4:5,6-di-O-isopropylidene-D-glucitol (85325-93-5,105454-09-9,105454-10-2) → (2S,3R)-3-[(R)-4-Azido-3-(tert-butyl-dimethyl-silanyloxy)-butyrylamino]-3-{(4S,5S)-5-[(2E,4E)-5-(4-ethoxy-phenyl)-penta-2,4-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester (645394-72-5)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 84 percent / BF₃*OEt₂ / tetrahydrofuran / -78 °C

2.1: hydrochloric acid / tetrahydrofuran

2.2: 67 percent / TsOH / acetone

3.1: 97 percent / 4-(dimethylamino)pyridine; triethylamine

4.1: 83 percent / NaN₃ / dimethylformamide / 120 °C

5.1: H₂ / Pd/C

6.1: pyridine

7.1: n-butyllithium / tetrahydrofuran / -78 °C

7.2: tetrahydrofuran

8.1: 4-(dimethylamino)pyridine; triethylamine

9.1: Na(Hg) / methanol

10.1: 87 percent / pyridinium p-toluenesulfonate / methanol / 45 °C

11.1: 92 percent / imidazole

12.1: 100 percent / diisopropylethylamine

13.1: 100 percent / Bu₄NF / tetrahydrofuran

14.1: 100 percent / NaBH₄ / ethanol

15.1: 96 percent / ethyl acetate / Heating

16.1: Dess-Martin periodinane

17.1: NaClO₂; resorcinol; NaH₂PO₄

18.1: 85 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; sodium azide; sodium amalgam; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; recorcinol; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; ethyl acetate; N,N-dimethyl-formamide; 16.1: Dess-Martin oxidation;

DOI:10.1002/anie.200352423

Reference yield:

3,4;5,6-di-O-isopropylidene-D-gluconic acid (52326-97-3) → (2S,3R)-3-[(R)-4-Azido-3-(tert-butyl-dimethyl-silanyloxy)-butyrylamino]-3-{(4S,5S)-5-[(2E,4E)-5-(4-ethoxy-phenyl)-penta-2,4-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester (645394-72-5)

Guidance literature:

Multi-step reaction with 21 steps

1.1: 100 percent / NaBH₄ / methanol

2.1: 85 percent / pyridine

3.1: 89 percent / K₂CO₃ / methanol

4.1: 84 percent / BF₃*OEt₂ / tetrahydrofuran / -78 °C

5.1: hydrochloric acid / tetrahydrofuran

5.2: 67 percent / TsOH / acetone

6.1: 97 percent / 4-(dimethylamino)pyridine; triethylamine

7.1: 83 percent / NaN₃ / dimethylformamide / 120 °C

8.1: H₂ / Pd/C

9.1: pyridine

10.1: n-butyllithium / tetrahydrofuran / -78 °C

10.2: tetrahydrofuran

11.1: 4-(dimethylamino)pyridine; triethylamine

12.1: Na(Hg) / methanol

13.1: 87 percent / pyridinium p-toluenesulfonate / methanol / 45 °C

14.1: 92 percent / imidazole

15.1: 100 percent / diisopropylethylamine

16.1: 100 percent / Bu₄NF / tetrahydrofuran

17.1: 100 percent / NaBH₄ / ethanol

18.1: 96 percent / ethyl acetate / Heating

19.1: Dess-Martin periodinane

20.1: NaClO₂; resorcinol; NaH₂PO₄

21.1: 85 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; sodium azide; sodium amalgam; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; recorcinol; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; ethyl acetate; N,N-dimethyl-formamide; 19.1: Dess-Martin oxidation;

DOI:10.1002/anie.200352423

Reference yield:

3,4:5,6-di-O-isopropylidene-1-O-p-tolylsulfonyl-D-glucitol (104527-46-0) → (2S,3R)-3-[(R)-4-Azido-3-(tert-butyl-dimethyl-silanyloxy)-butyrylamino]-3-{(4S,5S)-5-[(2E,4E)-5-(4-ethoxy-phenyl)-penta-2,4-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester (645394-72-5)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 89 percent / K₂CO₃ / methanol

2.1: 84 percent / BF₃*OEt₂ / tetrahydrofuran / -78 °C

3.1: hydrochloric acid / tetrahydrofuran

3.2: 67 percent / TsOH / acetone

4.1: 97 percent / 4-(dimethylamino)pyridine; triethylamine

5.1: 83 percent / NaN₃ / dimethylformamide / 120 °C

6.1: H₂ / Pd/C

7.1: pyridine

8.1: n-butyllithium / tetrahydrofuran / -78 °C

8.2: tetrahydrofuran

9.1: 4-(dimethylamino)pyridine; triethylamine

10.1: Na(Hg) / methanol

11.1: 87 percent / pyridinium p-toluenesulfonate / methanol / 45 °C

12.1: 92 percent / imidazole

13.1: 100 percent / diisopropylethylamine

14.1: 100 percent / Bu₄NF / tetrahydrofuran

15.1: 100 percent / NaBH₄ / ethanol

16.1: 96 percent / ethyl acetate / Heating

17.1: Dess-Martin periodinane

18.1: NaClO₂; resorcinol; NaH₂PO₄

19.1: 85 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; sodium azide; sodium amalgam; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; recorcinol; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; ethyl acetate; N,N-dimethyl-formamide; 17.1: Dess-Martin oxidation;

DOI:10.1002/anie.200352423

upstream raw materials:

1,2-anhydro-3,4:5,6-di-O-isopropylidene-D-glucitol

3,4;5,6-di-O-isopropylidene-D-gluconic acid

tert-butyldimethylsilyl chloride

3,4:5,6-di-O-isopropylidene-1-O-p-tolylsulfonyl-D-glucitol

Downstream raw materials:

C₅₁H₆₄N₈O₁₅

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