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

Base Information

Chemical Name:(1R,2R,3S,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-2-hydroxy-2'-(4-methoxyphenyl)-2,5'-dimethyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazole]-4-yl acetate
CAS No.:1403757-67-4
Molecular Formula:C₃₅H₄₁NO₇Si
Molecular Weight:615.799
Hs Code.:

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

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

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

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

There total 14 articles about (1R,2R,3S,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-2-hydroxy-2'-(4-methoxyphenyl)-2,5'-dimethyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazole]-4-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: 90.0%

: 1403757-66-3
(1R,2R,3S,4S,5R,5'S)-2-hydroxy-1-(hydroxymethyl)-2'-(4-methoxyphenyl)-2,5'-dimethyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazole]-4-yl acetate

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1403757-67-4
(1R,2R,3S,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-2-hydroxy-2'-(4-methoxyphenyl)-2,5'-dimethyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazole]-4-yl acetate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 4h; 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

: 1403757-67-4
(1R,2R,3S,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-2-hydroxy-2'-(4-methoxyphenyl)-2,5'-dimethyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazole]-4-yl acetate

Guidance literature:: Multi-step reaction with 8 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

7: 3-chloro-benzenecarboperoxoic acid / dichloromethane; water / 2 h / 0 °C

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

With dmap; tetrabutyl ammonium fluoride; (dimethylamino)trimethyltin; Dess-Martin periodane; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile;
DOI:10.1021/jo301638z

Reference yield:

: 1295471-52-1
C₃₉H₅₅NO₅Si₂

: 1403757-67-4
(1R,2R,3S,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-2-hydroxy-2'-(4-methoxyphenyl)-2,5'-dimethyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazole]-4-yl acetate

Guidance literature:: Multi-step reaction with 13 steps

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

2.1: ozone / dichloromethane / -78 °C

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

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

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

5.2: 1 h / 0 °C / Inert atmosphere

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

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

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

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

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

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

12.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane; water / 2 h / 0 °C

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

With pyridine; dmap; chloro-trimethyl-silane; oxalyl dichloride; cerium(III) chloride heptahydrate; tetrabutyl ammonium fluoride; titanium tetrachloride; (dimethylamino)trimethyltin; Dess-Martin periodane; ozone; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; trifluoroacetyl chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile;
DOI:10.1021/jo301638z