(4S,5S,6R,9S)-9-hydroxy-8-(hydroxymethyl)-2-(4-methoxyphenyl)-4,9-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-dien-6-yl acetate

Base Information

Chemical Name:(4S,5S,6R,9S)-9-hydroxy-8-(hydroxymethyl)-2-(4-methoxyphenyl)-4,9-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-dien-6-yl acetate
CAS No.:1403757-65-2
Molecular Formula:C₁₉H₂₃NO₆
Molecular Weight:361.395
Hs Code.:

Synonyms:(4S,5S,6R,9S)-9-hydroxy-8-(hydroxymethyl)-2-(4-methoxyphenyl)-4,9-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-dien-6-yl acetate

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Chemical Property of (4S,5S,6R,9S)-9-hydroxy-8-(hydroxymethyl)-2-(4-methoxyphenyl)-4,9-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-dien-6-yl acetate

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Technology Process of (4S,5S,6R,9S)-9-hydroxy-8-(hydroxymethyl)-2-(4-methoxyphenyl)-4,9-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-dien-6-yl acetate

There total 10 articles about (4S,5S,6R,9S)-9-hydroxy-8-(hydroxymethyl)-2-(4-methoxyphenyl)-4,9-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-dien-6-yl acetate 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: 85.0%

: 1403757-64-1
(4S,5S,6R,9S)-8-((tert-butyldiphenylsilyloxy)methyl)-9-hydroxy-2-(4-methoxyphenyl)-4,9-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-dien-6-yl acetate

: 1403757-65-2
(4S,5S,6R,9S)-9-hydroxy-8-(hydroxymethyl)-2-(4-methoxyphenyl)-4,9-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-dien-6-yl acetate

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 - 20 ℃; for 1h; Inert atmosphere;
DOI:10.1021/jo301638z

Reference yield:

: 1403757-58-3
(4S,5R,6R,9S)-8-((tert-butyldiphenylsilyloxy)methyl)-2-(4-methoxyphenyl)-4-methyl-9-(triethylsilyloxy)-3-oxa-1-azaspiro[4.4]nona-1,7-dien-6-ol

: 1403757-65-2
(4S,5S,6R,9S)-9-hydroxy-8-(hydroxymethyl)-2-(4-methoxyphenyl)-4,9-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-dien-6-yl acetate

Guidance literature:: Multi-step reaction with 6 steps

1: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

2: trifluoroacetic acid / acetonitrile; water / 72 h / 20 °C

3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

4: (dimethylamino)trimethyltin / tetrahydrofuran; diethyl ether / 0.83 h / -78 - 0 °C / Inert atmosphere

5: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

6: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

With dmap; tetrabutyl ammonium fluoride; (dimethylamino)trimethyltin; Dess-Martin periodane; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile;
DOI:10.1021/jo301638z

Reference yield:

: 1295471-02-1
C₄₅H₅₇NO₆Si₂

: 1403757-65-2
(4S,5S,6R,9S)-9-hydroxy-8-(hydroxymethyl)-2-(4-methoxyphenyl)-4,9-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-dien-6-yl acetate

Guidance literature:: Multi-step reaction with 13 steps

1.1: diisobutylaluminium hydride / dichloromethane / -78 °C

2.1: methylmagnesium bromide / diethyl ether / 0 °C

3.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 °C

4.1: ozone / dichloromethane / -78 °C

5.1: N-ethyl-N,N-diisopropylamine; titanium tetrachloride; chloro-trimethyl-silane / dichloromethane / 0 °C

6.1: trifluoroacetyl chloride; pyridine / dichloromethane / 20 °C

7.1: cerium(III) chloride heptahydrate / methanol; dichloromethane / 0.17 h / 0 °C / Inert atmosphere

7.2: 1 h / 0 °C / Inert atmosphere

8.1: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

9.1: trifluoroacetic acid / acetonitrile; water / 72 h / 20 °C

10.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

11.1: (dimethylamino)trimethyltin / tetrahydrofuran; diethyl ether / 0.83 h / -78 - 0 °C / Inert atmosphere

12.1: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

13.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; chloro-trimethyl-silane; oxalyl dichloride; cerium(III) chloride heptahydrate; methylmagnesium bromide; tetrabutyl ammonium fluoride; titanium tetrachloride; (dimethylamino)trimethyltin; diisobutylaluminium hydride; Dess-Martin periodane; ozone; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; trifluoroacetyl chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile;
DOI:10.1021/jo301638z