(S)-1-((1R,2R,3S,4S,5S)-1-amino-5-azido-3-((tertbutyldiphenylsilyloxy)methyl)-2,3-dihydroxy-2-methyl-4-(3-(prop-1-en-2-yl)phenylamino)cyclopentyl)ethyl dimethylcarbamate

Base Information

Chemical Name:(S)-1-((1R,2R,3S,4S,5S)-1-amino-5-azido-3-((tertbutyldiphenylsilyloxy)methyl)-2,3-dihydroxy-2-methyl-4-(3-(prop-1-en-2-yl)phenylamino)cyclopentyl)ethyl dimethylcarbamate
CAS No.:1403757-83-4
Molecular Formula:C₃₇H₅₀N₆O₅Si
Molecular Weight:686.927
Hs Code.:

(S)-1-((1R,2R,3S,4S,5S)-1-amino-5-azido-3-((tertbutyldiphenylsilyloxy)methyl)-2,3-dihydroxy-2-methyl-4-(3-(prop-1-en-2-yl)phenylamino)cyclopentyl)ethyl dimethylcarbamate

Synonyms:(S)-1-((1R,2R,3S,4S,5S)-1-amino-5-azido-3-((tertbutyldiphenylsilyloxy)methyl)-2,3-dihydroxy-2-methyl-4-(3-(prop-1-en-2-yl)phenylamino)cyclopentyl)ethyl dimethylcarbamate

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Chemical Property of (S)-1-((1R,2R,3S,4S,5S)-1-amino-5-azido-3-((tertbutyldiphenylsilyloxy)methyl)-2,3-dihydroxy-2-methyl-4-(3-(prop-1-en-2-yl)phenylamino)cyclopentyl)ethyl dimethylcarbamate

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Technology Process of (S)-1-((1R,2R,3S,4S,5S)-1-amino-5-azido-3-((tertbutyldiphenylsilyloxy)methyl)-2,3-dihydroxy-2-methyl-4-(3-(prop-1-en-2-yl)phenylamino)cyclopentyl)ethyl dimethylcarbamate

There total 25 articles about (S)-1-((1R,2R,3S,4S,5S)-1-amino-5-azido-3-((tertbutyldiphenylsilyloxy)methyl)-2,3-dihydroxy-2-methyl-4-(3-(prop-1-en-2-yl)phenylamino)cyclopentyl)ethyl dimethylcarbamate 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: 84.0%

: 1295471-69-0
C₃₄H₄₅N₅O₄Si

: 79-44-7
N,N-Dimethylcarbamoyl chloride

: 1403757-83-4
(S)-1-((1R,2R,3S,4S,5S)-1-amino-5-azido-3-((tertbutyldiphenylsilyloxy)methyl)-2,3-dihydroxy-2-methyl-4-(3-(prop-1-en-2-yl)phenylamino)cyclopentyl)ethyl dimethylcarbamate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;
DOI:10.1021/jo301638z

Reference yield:

: 1403757-80-1
(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

: 1403757-83-4
(S)-1-((1R,2R,3S,4S,5S)-1-amino-5-azido-3-((tertbutyldiphenylsilyloxy)methyl)-2,3-dihydroxy-2-methyl-4-(3-(prop-1-en-2-yl)phenylamino)cyclopentyl)ethyl dimethylcarbamate

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: diisobutylaluminium hydride / dichloromethane / -78 °C

10.1: triethylamine; dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; dmap; sodium periodate; osmium(VIII) oxide; water; 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;
DOI:10.1021/jo301638z

Reference yield:

: 1403757-81-2
(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

: 1403757-83-4
(S)-1-((1R,2R,3S,4S,5S)-1-amino-5-azido-3-((tertbutyldiphenylsilyloxy)methyl)-2,3-dihydroxy-2-methyl-4-(3-(prop-1-en-2-yl)phenylamino)cyclopentyl)ethyl dimethylcarbamate

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: diisobutylaluminium hydride / dichloromethane / -78 °C

9.1: triethylamine; dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; dmap; sodium periodate; osmium(VIII) oxide; water; 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;
DOI:10.1021/jo301638z