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

Base Information

Chemical Name:(1S,2R,3S,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-2-hydroxy-2'-(4-methoxyphenyl)-5'-methyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazole]-4-yl acetate
CAS No.:1403757-74-3
Molecular Formula:C₃₄H₃₉NO₇Si
Molecular Weight:601.772
Hs Code.:

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

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

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

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

There total 11 articles about (1S,2R,3S,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-2-hydroxy-2'-(4-methoxyphenyl)-5'-methyl-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: 88.0%

: 1403757-73-2
(1S,2R,3S,4S,5R,5'S)-2-hydroxy-1-(hydroxymethyl)-2'-(4-methoxyphenyl)-5'-methyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazole]-4-yl acetate

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1403757-74-3
(1S,2R,3S,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-2-hydroxy-2'-(4-methoxyphenyl)-5'-methyl-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

: 1403757-74-3
(1S,2R,3S,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-2-hydroxy-2'-(4-methoxyphenyl)-5'-methyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazole]-4-yl acetate

Guidance literature:: Multi-step reaction with 4 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

With dmap; tetrabutyl ammonium fluoride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo301638z

Reference yield:

: 1295471-53-2
C₃₈H₅₁NO₆Si₂

: 1403757-74-3
(1S,2R,3S,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-2-hydroxy-2'-(4-methoxyphenyl)-5'-methyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazole]-4-yl acetate

Guidance literature:: Multi-step reaction with 7 steps

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

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

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

3.2: 1 h / 0 °C / Inert atmosphere

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

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

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C / Inert atmosphere

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

With pyridine; dmap; chloro-trimethyl-silane; cerium(III) chloride heptahydrate; tetrabutyl ammonium fluoride; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetyl chloride; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo301638z