6-benzyl 8-methyl (6R)-3-[(tert-butyldiphenylsilyl)oxy]-9-hydroxy-7-azatricyclo[5.3.0.0^4,8]decane-6,8-dicarboxylate

Base Information

• Chemical Name: 6-benzyl 8-methyl (6R)-3-[(tert-butyldiphenylsilyl)oxy]-9-hydroxy-7-azatricyclo[5.3.0.0^4,8]decane-6,8-dicarboxylate
• CAS No.: 1449383-32-7
• Molecular Formula: C₃₅H₄₁NO₆Si
• Molecular Weight: 599.799

Synonyms:6-benzyl 8-methyl (6R)-3-[(tert-butyldiphenylsilyl)oxy]-9-hydroxy-7-azatricyclo[5.3.0.0^4,8]decane-6,8-dicarboxylate

Chemical Property of 6-benzyl 8-methyl (6R)-3-[(tert-butyldiphenylsilyl)oxy]-9-hydroxy-7-azatricyclo[5.3.0.0^4,8]decane-6,8-dicarboxylate

Chemical Property:

Purity/Quality:

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Technology Process of 6-benzyl 8-methyl (6R)-3-[(tert-butyldiphenylsilyl)oxy]-9-hydroxy-7-azatricyclo[5.3.0.0^4,8]decane-6,8-dicarboxylate

There total 12 articles about 6-benzyl 8-methyl (6R)-3-[(tert-butyldiphenylsilyl)oxy]-9-hydroxy-7-azatricyclo[5.3.0.0^4,8]decane-6,8-dicarboxylate 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: 86.0%

6-benzyl 8-methyl (6R)-3-[(tert-butyldiphenylsilyl)oxy]-9-oxo-7-azatricyclo[5.3.0.04,8]decane-6,8-dicarboxylate → 6-benzyl 8-methyl (6R)-3-[(tert-butyldiphenylsilyl)oxy]-9-hydroxy-7-azatricyclo[5.3.0.04,8]decane-6,8-dicarboxylate (1449383-32-7)

Guidance literature:

With sodium tetrahydroborate; In methanol; at -30 - 20 ℃; for 3h; diastereoselective reaction;

DOI:10.1016/j.tet.2013.03.104

Reference yield:

tert-butyl (4R,6S)-6-ethenyl-4-(2-methoxy-2-oxoethyl)-2-oxo-1,3-oxazinane-3-carboxylate → 6-benzyl 8-methyl (6R)-3-[(tert-butyldiphenylsilyl)oxy]-9-hydroxy-7-azatricyclo[5.3.0.04,8]decane-6,8-dicarboxylate (1449383-32-7)

Guidance literature:

Multi-step reaction with 7 steps

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

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

2.2: 2 h / 0 - 20 °C

2.3: 20 °C

3.1: 1H-imidazole / dichloromethane

4.1: dichloromethane / 2 h / 0 - 20 °C

5.1: triethylamine / dichloromethane / 0 - 20 °C / Molecular sieve

5.2: 12 h / 20 °C

6.1: dirhodium tetraacetate / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / Reflux

7.1: sodium tetrahydroborate / methanol / 3 h / -30 - 20 °C

With 1H-imidazole; dirhodium tetraacetate; sodium tetrahydroborate; caesium carbonate; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane;

DOI:10.1016/j.tet.2013.03.104

Reference yield:

methyl 2-[(6S)-6-ethenyl-2-oxo-1,3-oxazinan-4-yl]acetate → 6-benzyl 8-methyl (6R)-3-[(tert-butyldiphenylsilyl)oxy]-9-hydroxy-7-azatricyclo[5.3.0.04,8]decane-6,8-dicarboxylate (1449383-32-7)

Guidance literature:

Multi-step reaction with 8 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: dichloromethane / 2 h / 0 - 20 °C

6.1: triethylamine / dichloromethane / 0 - 20 °C / Molecular sieve

6.2: 12 h / 20 °C

7.1: dirhodium tetraacetate / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / Reflux

8.1: sodium tetrahydroborate / methanol / 3 h / -30 - 20 °C

With 1H-imidazole; dmap; dirhodium tetraacetate; sodium tetrahydroborate; caesium carbonate; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane;

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

benzylglyoxylate

Downstream raw materials:

C₂₈H₃₃NO₆Si

C₂₆H₃₁NO₃Si

C₂₉H₃₇NO₂Si

4-benzyl 2-methyl (4R)-7-[(tert-butyldiphenylsilyl)oxy]-11-oxa-3-azatetracyclo[5.3.1.0^2,6.0^3,9]undecane-2,4-dicarboxylate

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