(1R,3R,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-4-hydroxy-2'-(4-methoxyphenyl)-5'-methyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazol]-2-one

Base Information

Chemical Name:(1R,3R,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-4-hydroxy-2'-(4-methoxyphenyl)-5'-methyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazol]-2-one
CAS No.:1403757-77-6
Molecular Formula:C₃₂H₃₅NO₆Si
Molecular Weight:557.719
Hs Code.:

Synonyms:(1R,3R,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-4-hydroxy-2'-(4-methoxyphenyl)-5'-methyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazol]-2-one

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Chemical Property of (1R,3R,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-4-hydroxy-2'-(4-methoxyphenyl)-5'-methyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazol]-2-one

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Technology Process of (1R,3R,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-4-hydroxy-2'-(4-methoxyphenyl)-5'-methyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazol]-2-one

There total 13 articles about (1R,3R,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-4-hydroxy-2'-(4-methoxyphenyl)-5'-methyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazol]-2-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: 87.0%

: 1403757-75-4
(1R,3S,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-2'-(4-methoxyphenyl)-5'-methyl-2-oxo-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazole]-4-yl acetate

: 1403757-77-6
(1R,3R,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-4-hydroxy-2'-(4-methoxyphenyl)-5'-methyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazol]-2-one

Guidance literature:: With (dimethylamino)trimethyltin; In toluene; at 20 ℃; for 3h; 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

: 1403757-77-6
(1R,3R,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-4-hydroxy-2'-(4-methoxyphenyl)-5'-methyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazol]-2-one

Guidance literature:: Multi-step reaction with 6 steps

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

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere

3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C / Inert atmosphere

4: triethylamine; dmap / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

5: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

6: (dimethylamino)trimethyltin / toluene / 3 h / 20 °C / Inert atmosphere

With dmap; tetrabutyl ammonium fluoride; (dimethylamino)trimethyltin; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo301638z

Reference yield:

: C₃₈H₅₁NO₅Si₂

: 1403757-77-6
(1R,3R,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-4-hydroxy-2'-(4-methoxyphenyl)-5'-methyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazol]-2-one

Guidance literature:: Multi-step reaction with 12 steps

1.1: methylmagnesium bromide / diethyl ether / 0 °C

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

3.1: ozone / dichloromethane / -78 °C

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

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

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

6.2: 1 h / 0 °C / Inert atmosphere

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

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere

9.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C / Inert atmosphere

10.1: triethylamine; dmap / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

11.1: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

12.1: (dimethylamino)trimethyltin / toluene / 3 h / 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; Dess-Martin periodane; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetyl chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo301638z