(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

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)ethyl 4-methoxybenzoate
CAS No.:1403757-84-5
Molecular Formula:C₅₆H₆₃N₅O₆Si
Molecular Weight:930.232
Hs Code.:

(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

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)ethyl 4-methoxybenzoate

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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)ethyl 4-methoxybenzoate

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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)ethyl 4-methoxybenzoate

There total 24 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)ethyl 4-methoxybenzoate 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: 80.0%

: 1295471-26-9
C₄₂H₅₁N₅O₆Si

: 100-39-0
benzyl bromide

: 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)ethyl 4-methoxybenzoate

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 2h;
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

: 1403757-84-5
(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)ethyl 4-methoxybenzoate

Guidance literature:: Multi-step reaction with 9 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

With pyridine; hydrogenchloride; dmap; sodium periodate; osmium(VIII) oxide; water; tetra-(n-butyl)ammonium iodide; sodium 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; mineral oil;
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

: 1403757-84-5
(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)ethyl 4-methoxybenzoate

Guidance literature:: Multi-step reaction with 8 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

With pyridine; hydrogenchloride; dmap; sodium periodate; osmium(VIII) oxide; water; tetra-(n-butyl)ammonium iodide; sodium 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; mineral oil;
DOI:10.1021/jo301638z