(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

Base Information

Chemical Name:(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
CAS No.:1403757-73-2
Molecular Formula:C₁₈H₂₁NO₇
Molecular Weight:363.367
Hs Code.:

Synonyms:(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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (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

There total 11 articles about (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 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: 64.0%

: 1403757-72-1
(4S,5S,6R,9S)-9-hydroxy-8-(hydroxymethyl)-2-(4-methoxyphenyl)-4-methyl-3-oxa-1-azaspiro[4.4]nona-1,7-dien-6-yl acetate

: 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

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 2h; 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

: 1403757-73-2
(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

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

: 1295471-52-1
C₃₉H₅₅NO₅Si₂

: 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

Guidance literature:: Multi-step reaction with 8 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: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere

8.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C / Inert atmosphere

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