(2S,3aR,8R,8aS)-1-benzyl 2-methyl 8-((tert-butyldimethylsilyl)oxy)-4-oxo-2,3,3a,4,8,8a-hexahydro-1H-oxepino[4,3-b]pyrrole-1,2-dicarboxylate

Base Information

Chemical Name:(2S,3aR,8R,8aS)-1-benzyl 2-methyl 8-((tert-butyldimethylsilyl)oxy)-4-oxo-2,3,3a,4,8,8a-hexahydro-1H-oxepino[4,3-b]pyrrole-1,2-dicarboxylate
CAS No.:1421232-56-5
Molecular Formula:C₂₄H₃₃NO₇Si
Molecular Weight:475.614
Hs Code.:

Synonyms:(2S,3aR,8R,8aS)-1-benzyl 2-methyl 8-((tert-butyldimethylsilyl)oxy)-4-oxo-2,3,3a,4,8,8a-hexahydro-1H-oxepino[4,3-b]pyrrole-1,2-dicarboxylate

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Chemical Property of (2S,3aR,8R,8aS)-1-benzyl 2-methyl 8-((tert-butyldimethylsilyl)oxy)-4-oxo-2,3,3a,4,8,8a-hexahydro-1H-oxepino[4,3-b]pyrrole-1,2-dicarboxylate

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Technology Process of (2S,3aR,8R,8aS)-1-benzyl 2-methyl 8-((tert-butyldimethylsilyl)oxy)-4-oxo-2,3,3a,4,8,8a-hexahydro-1H-oxepino[4,3-b]pyrrole-1,2-dicarboxylate

There total 9 articles about (2S,3aR,8R,8aS)-1-benzyl 2-methyl 8-((tert-butyldimethylsilyl)oxy)-4-oxo-2,3,3a,4,8,8a-hexahydro-1H-oxepino[4,3-b]pyrrole-1,2-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: 53.0%

: 1421232-55-4
(2S,3aR,7R,7aS)-1-benzyl 2-methyl 7-((tert-butyldimethylsilyl)oxy)-4-oxo-2,3,3a,4,7,7a-hexahydro-1H-indole-1,2-dicarboxylate

: 1421232-56-5
(2S,3aR,8R,8aS)-1-benzyl 2-methyl 8-((tert-butyldimethylsilyl)oxy)-4-oxo-2,3,3a,4,8,8a-hexahydro-1H-oxepino[4,3-b]pyrrole-1,2-dicarboxylate

Guidance literature:: With urea hydrogen peroxide adduct; trifluoroacetic anhydride; In dichloromethane; at -20 ℃; for 10h; Inert atmosphere;
DOI:10.1002/anie.201207307

Reference yield:

: 320748-59-2
(2S,7aR)-6-oxo-2,3,5,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 1421232-56-5
(2S,3aR,8R,8aS)-1-benzyl 2-methyl 8-((tert-butyldimethylsilyl)oxy)-4-oxo-2,3,3a,4,8,8a-hexahydro-1H-oxepino[4,3-b]pyrrole-1,2-dicarboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.75 h / 20 °C

2.1: dihydrogen peroxide / methanol; water / 0.08 h / 0 °C

2.2: 0.25 h / 0 °C

3.1: hydrazine hydrate; acetic acid / dichloromethane / 11 h / 0 - 20 °C

4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 0 °C

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

6.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 0.5 h / -78 °C

7.1: silica gel / dichloromethane

8.1: 2,6-dimethylpyridine / dichloromethane / 0.42 h / 0 °C / Inert atmosphere

9.1: trifluoroacetic anhydride; urea hydrogen peroxide adduct / dichloromethane / 10 h / -20 °C / Inert atmosphere

With 2,6-dimethylpyridine; dihydrogen peroxide; 3,3-dimethyldioxirane; urea hydrogen peroxide adduct; silica gel; sodium hydrogencarbonate; Dess-Martin periodane; hydrazine hydrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; In methanol; dichloromethane; water; acetone; 3.1: |Wharton Fragmentation / 4.1: |Dess-Martin Oxidation / 7.1: |Wharton Fragmentation / 9.1: |Baeyer-Villiger Ketone Oxidation;
DOI:10.1002/anie.201207307

Reference yield:

: 1421232-64-5
(2S,3aS,7aR)-1-benzyl 2-methyl 6-oxo-3,3a,7,7a-tetrahydro-1H-indole-1,2(2H,6H)-dicarboxylate

: 1421232-56-5
(2S,3aR,8R,8aS)-1-benzyl 2-methyl 8-((tert-butyldimethylsilyl)oxy)-4-oxo-2,3,3a,4,8,8a-hexahydro-1H-oxepino[4,3-b]pyrrole-1,2-dicarboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: dihydrogen peroxide / methanol; water / 0.08 h / 0 °C

1.2: 0.25 h / 0 °C

2.1: hydrazine hydrate; acetic acid / dichloromethane / 11 h / 0 - 20 °C

3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 0 °C

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

5.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 0.5 h / -78 °C

6.1: silica gel / dichloromethane

7.1: 2,6-dimethylpyridine / dichloromethane / 0.42 h / 0 °C / Inert atmosphere

8.1: trifluoroacetic anhydride; urea hydrogen peroxide adduct / dichloromethane / 10 h / -20 °C / Inert atmosphere

With 2,6-dimethylpyridine; dihydrogen peroxide; 3,3-dimethyldioxirane; urea hydrogen peroxide adduct; silica gel; sodium hydrogencarbonate; Dess-Martin periodane; hydrazine hydrate; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; In methanol; dichloromethane; water; acetone; 2.1: |Wharton Fragmentation / 3.1: |Dess-Martin Oxidation / 6.1: |Wharton Fragmentation / 8.1: |Baeyer-Villiger Ketone Oxidation;
DOI:10.1002/anie.201207307