(1R,2R,3R,5S,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'-oxazol]-4-one

Base Information

• Chemical Name: (1R,2R,3R,5S,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'-oxazol]-4-one
• CAS No.: 1403757-69-6
• Molecular Formula: C₃₃H₃₇NO₆Si
• Molecular Weight: 571.745

Synonyms:(1R,2R,3R,5S,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'-oxazol]-4-one

Chemical Property of (1R,2R,3R,5S,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'-oxazol]-4-one

Chemical Property:

Purity/Quality:

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Technology Process of (1R,2R,3R,5S,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'-oxazol]-4-one

There total 18 articles about (1R,2R,3R,5S,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'-oxazol]-4-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: 92.0%

(1R,2R,3R,4S,5R,5'S)-1-((tert-butyldiphenylsilyloxy)methyl)-2'-(4-methoxyphenyl)-2,5'-dimethyl-5'H-6-oxaspiro[bicyclo[3.1.0]hexane-3,4'-oxazole]-2,4-diol (1403757-68-5) → (1R,2R,3R,5S,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'-oxazol]-4-one (1403757-69-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jo301638z

Reference yield:

(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 (1403757-58-3) → (1R,2R,3R,5S,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'-oxazol]-4-one (1403757-69-6)

Guidance literature:

Multi-step reaction with 10 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

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

10: Dess-Martin periodane / dichloromethane / 2 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; toluene; acetonitrile;

DOI:10.1021/jo301638z

Reference yield:

C39H55NO5Si2 (1295471-52-1) → (1R,2R,3R,5S,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'-oxazol]-4-one (1403757-69-6)

Guidance literature:

Multi-step reaction with 15 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

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

15.1: Dess-Martin periodane / dichloromethane / 2 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; toluene; acetonitrile;

DOI:10.1021/jo301638z

upstream raw materials:

(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

(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

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

(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

Downstream raw materials:

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

(4S,5R,6R,7S,8S,9S)-7-((tert-butyldiphenylsilyloxy)methyl)-2-(4-methoxyphenyl)-4,6-dimethyl-8-(3-(prop-1-en-2-yl)phenylamino)-3-oxa-1-azaspiro[4.4]non-1-ene-6,7,9-triol

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