methyl 3-[(tert-butyldiphenylsilyl)oxy]-9-oxo-7-azatricyclo[5.3.0.0^4,8]decane-8-carboxylate

Base Information

• Chemical Name: methyl 3-[(tert-butyldiphenylsilyl)oxy]-9-oxo-7-azatricyclo[5.3.0.0^4,8]decane-8-carboxylate
• CAS No.: 1449383-29-2
• Molecular Formula: C₂₇H₃₃NO₄Si
• Molecular Weight: 463.649

Synonyms:methyl 3-[(tert-butyldiphenylsilyl)oxy]-9-oxo-7-azatricyclo[5.3.0.0^4,8]decane-8-carboxylate

Chemical Property of methyl 3-[(tert-butyldiphenylsilyl)oxy]-9-oxo-7-azatricyclo[5.3.0.0^4,8]decane-8-carboxylate

Chemical Property:

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Technology Process of methyl 3-[(tert-butyldiphenylsilyl)oxy]-9-oxo-7-azatricyclo[5.3.0.0^4,8]decane-8-carboxylate

There total 9 articles about methyl 3-[(tert-butyldiphenylsilyl)oxy]-9-oxo-7-azatricyclo[5.3.0.0^4,8]decane-8-carboxylate 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: 32.0%

methyl (5R)-5-[(2S)-2-[(tert-butyldiphenylsilyl)oxy]but-3-en-1-yl]-7-oxo-hexahydropyrrolo[1,2-c][1,3]oxazole-7a-carboxylate → methyl 3-[(tert-butyldiphenylsilyl)oxy]-9-oxo-7-azatricyclo[5.3.0.04,8]decane-8-carboxylate (1449383-29-2) + C27H33NO4Si (1449383-30-5)

Guidance literature:

In toluene; at 160 ℃; for 4h; Sealed tube;

DOI:10.1016/j.tet.2013.03.104

Reference yield:

methyl 2-[(6S)-6-ethenyl-2-oxo-1,3-oxazinan-4-yl]acetate → methyl 3-[(tert-butyldiphenylsilyl)oxy]-9-oxo-7-azatricyclo[5.3.0.04,8]decane-8-carboxylate (1449383-29-2) + C27H33NO4Si (1449383-30-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: triethylamine; dmap / dichloromethane / 20 °C

2.1: caesium carbonate / methanol / 24 h / 20 °C

3.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C

3.2: 2 h / 0 - 20 °C

3.3: 20 °C

4.1: 1H-imidazole / dichloromethane

5.1: dirhodium tetraacetate / dichloromethane / 16 h / 20 °C

6.1: trifluoroacetic acid / dichloromethane / 6 h / 20 °C

7.1: toluene / 4 h / 160 °C / Sealed tube

With 1H-imidazole; dmap; dirhodium tetraacetate; caesium carbonate; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1016/j.tet.2013.03.104

Reference yield:

C13H23NO5 (1449383-24-7) → methyl 3-[(tert-butyldiphenylsilyl)oxy]-9-oxo-7-azatricyclo[5.3.0.04,8]decane-8-carboxylate (1449383-29-2) + C27H33NO4Si (1449383-30-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C

1.2: 2 h / 0 - 20 °C

1.3: 20 °C

2.1: 1H-imidazole / dichloromethane

3.1: dirhodium tetraacetate / dichloromethane / 16 h / 20 °C

4.1: trifluoroacetic acid / dichloromethane / 6 h / 20 °C

5.1: toluene / 4 h / 160 °C / Sealed tube

With 1H-imidazole; dirhodium tetraacetate; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.tet.2013.03.104

upstream raw materials:

C₁₃H₂₃NO₅

tert-butylchlorodiphenylsilane

(5R,7S)-methyl 5-(tert-butoxycarbonylamino)-2-diazo-7-hydroxy-3-oxonon-8-enoate

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