(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)ethanol

Base Information

• Chemical Name: (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)ethanol
• CAS No.: 1403757-85-6
• Molecular Formula: C₄₈H₅₇N₅O₄Si
• Molecular Weight: 796.097

Synonyms:(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)ethanol

Chemical Property of (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)ethanol

Chemical Property:

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Technology Process of (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)ethanol

There total 25 articles about (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)ethanol 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: 92.0%

(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 (1403757-84-5) → (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)ethanol (1403757-85-6)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 1.5h; Inert atmosphere;

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) → (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)ethanol (1403757-85-6)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; hydrogenchloride; dmap; sodium periodate; osmium(VIII) oxide; water; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; 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) → (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)ethanol (1403757-85-6)

Guidance literature:

Multi-step reaction with 10 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

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:

(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 dimethylcarbamate

(1S,2S,3R,4R,5S)-2-azido-4-(benzyloxy)-3-((S)-1-(benzyloxy)ethyl)-5-(benzyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-4-methyl-N₁-(3-(prop-1-en-2-yl)phenyl)cyclopentane-1,3-diamine

N-((1S,2S,3R,4R,5S)-5-azido-3-(benzyloxy)-4-((S)-1-(benzyloxy)ethyl)-2-(benzyloxymethyl)-2-(tert-butyldiphenylsilyloxy)-4-isocyanato-3-methylcyclopentyl)-3-(prop-1-en-2-yl)aniline

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

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