(1S,5R,6S,7S,8R)-6-azido-1-((tert-butyldiphenylsilyloxy)-methyl)-8-hydroxy-5-((S)-1-hydroxyethyl)-8-methyl-7-(3-(prop-1-en-2-yl)phenylamino)-2-oxa-4-azabicyclo[3.2.1]octan-3-one

Base Information

Chemical Name:(1S,5R,6S,7S,8R)-6-azido-1-((tert-butyldiphenylsilyloxy)-methyl)-8-hydroxy-5-((S)-1-hydroxyethyl)-8-methyl-7-(3-(prop-1-en-2-yl)phenylamino)-2-oxa-4-azabicyclo[3.2.1]octan-3-one
CAS No.:1403834-91-2
Molecular Formula:C₃₅H₄₃N₅O₅Si
Molecular Weight:641.842
Hs Code.:

(1S,5R,6S,7S,8R)-6-azido-1-((tert-butyldiphenylsilyloxy)-methyl)-8-hydroxy-5-((S)-1-hydroxyethyl)-8-methyl-7-(3-(prop-1-en-2-yl)phenylamino)-2-oxa-4-azabicyclo[3.2.1]octan-3-one

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Chemical Property of (1S,5R,6S,7S,8R)-6-azido-1-((tert-butyldiphenylsilyloxy)-methyl)-8-hydroxy-5-((S)-1-hydroxyethyl)-8-methyl-7-(3-(prop-1-en-2-yl)phenylamino)-2-oxa-4-azabicyclo[3.2.1]octan-3-one

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Technology Process of (1S,5R,6S,7S,8R)-6-azido-1-((tert-butyldiphenylsilyloxy)-methyl)-8-hydroxy-5-((S)-1-hydroxyethyl)-8-methyl-7-(3-(prop-1-en-2-yl)phenylamino)-2-oxa-4-azabicyclo[3.2.1]octan-3-one

There total 23 articles about (1S,5R,6S,7S,8R)-6-azido-1-((tert-butyldiphenylsilyloxy)-methyl)-8-hydroxy-5-((S)-1-hydroxyethyl)-8-methyl-7-(3-(prop-1-en-2-yl)phenylamino)-2-oxa-4-azabicyclo[3.2.1]octan-3-one 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:

: 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

: 1403834-91-2
(1S,5R,6S,7S,8R)-6-azido-1-((tert-butyldiphenylsilyloxy)-methyl)-8-hydroxy-5-((S)-1-hydroxyethyl)-8-methyl-7-(3-(prop-1-en-2-yl)phenylamino)-2-oxa-4-azabicyclo[3.2.1]octan-3-one

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: pyrographite; triethylamine / tetrahydrofuran / -46 °C

10.1: (dimethylamino)trimethyltin / toluene / 3 h / Inert atmosphere; Reflux

With pyridine; hydrogenchloride; dmap; sodium periodate; osmium(VIII) oxide; water; (dimethylamino)trimethyltin; 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;
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

: 1403834-91-2
(1S,5R,6S,7S,8R)-6-azido-1-((tert-butyldiphenylsilyloxy)-methyl)-8-hydroxy-5-((S)-1-hydroxyethyl)-8-methyl-7-(3-(prop-1-en-2-yl)phenylamino)-2-oxa-4-azabicyclo[3.2.1]octan-3-one

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: pyrographite; triethylamine / tetrahydrofuran / -46 °C

9.1: (dimethylamino)trimethyltin / toluene / 3 h / Inert atmosphere; Reflux

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

Reference yield:

: 1403757-82-3
(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

: 1403834-91-2
(1S,5R,6S,7S,8R)-6-azido-1-((tert-butyldiphenylsilyloxy)-methyl)-8-hydroxy-5-((S)-1-hydroxyethyl)-8-methyl-7-(3-(prop-1-en-2-yl)phenylamino)-2-oxa-4-azabicyclo[3.2.1]octan-3-one

Guidance literature:: Multi-step reaction with 7 steps

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

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

2.2: 20 °C

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

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

5.1: hydrogenchloride / water; tetrahydrofuran / 20 °C

6.1: pyrographite; triethylamine / tetrahydrofuran / -46 °C

7.1: (dimethylamino)trimethyltin / toluene / 3 h / Inert atmosphere; Reflux

With pyridine; hydrogenchloride; dmap; (dimethylamino)trimethyltin; pyrographite; ammonium chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; N,N-Dimethylcarbamoyl chloride; zinc; In tetrahydrofuran; ethanol; dichloromethane; water; toluene;
DOI:10.1021/jo301638z