(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

Base Information

• Chemical Name: (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
• CAS No.: 1403757-87-8
• Molecular Formula: C₅₅H₆₃N₅O₄Si
• Molecular Weight: 886.222

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (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

There total 25 articles about (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 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: 78.0%

(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)ethanol (1403757-85-6) + benzyl bromide (100-39-0) → (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 (1403757-87-8)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 3h;

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) → (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 (1403757-87-8)

Guidance literature:

Multi-step reaction with 10 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

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) → (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 (1403757-87-8)

Guidance literature:

Multi-step reaction with 11 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

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:

(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

benzyl bromide

(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

Downstream raw materials:

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

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

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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