3-((1R,2R,3S,4S,5S)-4-(3-acetylphenylamino)-5-azido-2-(benzyloxy)-1-((S)-1-(benzyloxy)ethyl)-3-(benzyloxymethyl)-3-(tert-butyldiphenylsilyloxy)-2-methylcyclopentyl)-1,1-dimethylurea

Base Information

• Chemical Name: 3-((1R,2R,3S,4S,5S)-4-(3-acetylphenylamino)-5-azido-2-(benzyloxy)-1-((S)-1-(benzyloxy)ethyl)-3-(benzyloxymethyl)-3-(tert-butyldiphenylsilyloxy)-2-methylcyclopentyl)-1,1-dimethylurea
• CAS No.: 1403757-90-3
• Molecular Formula: C₅₇H₆₆N₆O₆Si
• Molecular Weight: 959.273

Synonyms:3-((1R,2R,3S,4S,5S)-4-(3-acetylphenylamino)-5-azido-2-(benzyloxy)-1-((S)-1-(benzyloxy)ethyl)-3-(benzyloxymethyl)-3-(tert-butyldiphenylsilyloxy)-2-methylcyclopentyl)-1,1-dimethylurea

Chemical Property of 3-((1R,2R,3S,4S,5S)-4-(3-acetylphenylamino)-5-azido-2-(benzyloxy)-1-((S)-1-(benzyloxy)ethyl)-3-(benzyloxymethyl)-3-(tert-butyldiphenylsilyloxy)-2-methylcyclopentyl)-1,1-dimethylurea

Chemical Property:

Purity/Quality:

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Technology Process of 3-((1R,2R,3S,4S,5S)-4-(3-acetylphenylamino)-5-azido-2-(benzyloxy)-1-((S)-1-(benzyloxy)ethyl)-3-(benzyloxymethyl)-3-(tert-butyldiphenylsilyloxy)-2-methylcyclopentyl)-1,1-dimethylurea

There total 27 articles about 3-((1R,2R,3S,4S,5S)-4-(3-acetylphenylamino)-5-azido-2-(benzyloxy)-1-((S)-1-(benzyloxy)ethyl)-3-(benzyloxymethyl)-3-(tert-butyldiphenylsilyloxy)-2-methylcyclopentyl)-1,1-dimethylurea 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:

C58H70N6O7Si → 3-((1R,2R,3S,4S,5S)-4-(3-acetylphenylamino)-5-azido-2-(benzyloxy)-1-((S)-1-(benzyloxy)ethyl)-3-(benzyloxymethyl)-3-(tert-butyldiphenylsilyloxy)-2-methylcyclopentyl)-1,1-dimethylurea (1403757-90-3)

Guidance literature:

With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 2h;

DOI:10.1021/jo301638z

Reference yield:

(4S,5R,6R,7S,8S,9S)-9-azido-7-((tert-butyldiphenylsilyloxy)-methyl)-6,7-dihydroxy-1-(4-methoxybenzyl)-4,6-dimethyl-8-(3-(prop-1-en-2-yl)phenylamino)-3-oxa-1-azaspiro[4.4]nonan-2-one (1403757-81-2) → 3-((1R,2R,3S,4S,5S)-4-(3-acetylphenylamino)-5-azido-2-(benzyloxy)-1-((S)-1-(benzyloxy)ethyl)-3-(benzyloxymethyl)-3-(tert-butyldiphenylsilyloxy)-2-methylcyclopentyl)-1,1-dimethylurea (1403757-90-3)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide; water / acetone; tetrahydrofuran / 2 h / 20 °C

2.1: sodium periodate / water; tetrahydrofuran / 3 h / 20 °C

3.1: trifluoroacetic acid / neat (no solvent) / 40 °C

4.1: pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane; tetrahydrofuran / 20 °C

4.2: 20 °C

5.1: ammonium chloride; zinc / water; tetrahydrofuran; ethanol / 20 °C

6.1: N,N-Dimethylcarbamoyl chloride; triethylamine; dmap / dichloromethane / 20 °C

7.1: hydrogenchloride / water; tetrahydrofuran / 20 °C

8.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C

9.1: tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride / dichloromethane; toluene / 1.5 h / -78 °C / Inert atmosphere

10.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran; mineral oil / 3 h / 0 - 20 °C

11.1: pyrographite; triethylamine / tetrahydrofuran / 0.33 h / -46 °C / Inert atmosphere

12.1: neat (no solvent) / -46 - 20 °C

13.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide; water / acetone; tetrahydrofuran / 2 h / 0 - 20 °C

14.1: sodium periodate / water; tetrahydrofuran / 2 h / 20 °C

With pyridine; hydrogenchloride; dmap; sodium periodate; osmium(VIII) oxide; water; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; pyrographite; ammonium chloride; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; N,N-Dimethylcarbamoyl chloride; zinc; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; toluene; mineral oil;

DOI:10.1021/jo301638z

Reference yield:

(1S,2R,3R,4S,5S)-4-azido-1-((tert-butyldiphenylsilyloxy)-methyl)-3-((S)-1-hydroxyethyl)-3-(4-methoxybenzylamino)-2-methyl-5-(3-(prop-1-en-2-yl)phenylamino)cyclopentane-1,2-diol (1403757-80-1) → 3-((1R,2R,3S,4S,5S)-4-(3-acetylphenylamino)-5-azido-2-(benzyloxy)-1-((S)-1-(benzyloxy)ethyl)-3-(benzyloxymethyl)-3-(tert-butyldiphenylsilyloxy)-2-methylcyclopentyl)-1,1-dimethylurea (1403757-90-3)

Guidance literature:

Multi-step reaction with 15 steps

1.1: pyrographite; triethylamine / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

2.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide; water / acetone; tetrahydrofuran / 2 h / 20 °C

3.1: sodium periodate / water; tetrahydrofuran / 3 h / 20 °C

4.1: trifluoroacetic acid / neat (no solvent) / 40 °C

5.1: pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane; tetrahydrofuran / 20 °C

5.2: 20 °C

6.1: ammonium chloride; zinc / water; tetrahydrofuran; ethanol / 20 °C

7.1: N,N-Dimethylcarbamoyl chloride; triethylamine; dmap / dichloromethane / 20 °C

8.1: hydrogenchloride / water; tetrahydrofuran / 20 °C

9.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C

10.1: tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride / dichloromethane; toluene / 1.5 h / -78 °C / Inert atmosphere

11.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran; mineral oil / 3 h / 0 - 20 °C

12.1: pyrographite; triethylamine / tetrahydrofuran / 0.33 h / -46 °C / Inert atmosphere

13.1: neat (no solvent) / -46 - 20 °C

14.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide; water / acetone; tetrahydrofuran / 2 h / 0 - 20 °C

15.1: sodium periodate / water; tetrahydrofuran / 2 h / 20 °C

With pyridine; hydrogenchloride; dmap; sodium periodate; osmium(VIII) oxide; water; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; pyrographite; ammonium chloride; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; N,N-Dimethylcarbamoyl chloride; zinc; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; toluene; mineral oil;

DOI:10.1021/jo301638z

upstream raw materials:

(1S,2R,3R,4S,5S)-4-azido-1-((tert-butyldiphenylsilyloxy)-methyl)-3-((S)-1-hydroxyethyl)-3-(4-methoxybenzylamino)-2-methyl-5-(3-(prop-1-en-2-yl)phenylamino)cyclopentane-1,2-diol

(4S,5R,6R,7S,8S,9S)-9-azido-7-((tert-butyldiphenylsilyloxy)-methyl)-6,7-dihydroxy-1-(4-methoxybenzyl)-4,6-dimethyl-8-(3-(prop-1-en-2-yl)phenylamino)-3-oxa-1-azaspiro[4.4]nonan-2-one

(4S,5R,6R,7S,8S,9S)-8-(3-acetylphenylamino)-9-azido-7-((tert-butyldiphenylsilyloxy)methyl)-6,7-dihydroxy-1-(4-methoxybenzyl)-4,6-dimethyl-3-oxa-1-azaspiro[4.4]nonan-2-one

(S)-1-((1R,2R,3S,4S,5S)-1-amino-5-azido-2-(benzyloxy)-3-(benzyloxymethyl)-3-(tert-butyldiphenylsilyloxy)-2-methyl-4-(3-(prop-1-en-2-yl)phenylamino)cyclopentyl)ethyl 4-methoxybenzoate

Downstream raw materials:

3-((1R,2R,3S,4S,5S)-4-(3-acetylphenylamino)-5-azido-2-(benzyloxy)-1-((S)-1-(benzyloxy)ethyl)-3-(benzyloxymethyl)-3-hydroxy-2-methylcyclopentyl)-1,1-dimethylurea

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