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

Base Information

• Chemical Name: (2S,8R,8aS)-1-benzyl 2-methyl 8-((tert-butyldimethylsilyl)oxy)-2,3,8,8a-tetrahydro-1H-oxepino[4,3-b]pyrrole-1,2-dicarboxylate
• CAS No.: 1421232-58-7
• Molecular Formula: C₂₄H₃₃NO₆Si
• Molecular Weight: 459.615
• Mol file: 1421232-58-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (2S,8R,8aS)-1-benzyl 2-methyl 8-((tert-butyldimethylsilyl)oxy)-2,3,8,8a-tetrahydro-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: 94.0%

(2S,8R,8aS)-1-benzyl 2-methyl 8-((tert-butyldimethylsilyl)oxy)-4-(((trifluoromethyl)sulfonyl)oxy)-2,3,8,8a-tetrahydro-1H-oxepino[4,3-b]pyrrole-1,2-dicarboxylate (1421232-57-6) → (2S,8R,8aS)-1-benzyl 2-methyl 8-((tert-butyldimethylsilyl)oxy)-2,3,8,8a-tetrahydro-1H-oxepino[4,3-b]pyrrole-1,2-dicarboxylate (1421232-58-7)

Guidance literature:

With formic acid; tributyl-amine; palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 65 ℃; for 0.25h;

DOI:10.1002/anie.201207307

Reference yield:

(2S,7aR)-6-oxo-2,3,5,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (320748-59-2) → (2S,8R,8aS)-1-benzyl 2-methyl 8-((tert-butyldimethylsilyl)oxy)-2,3,8,8a-tetrahydro-1H-oxepino[4,3-b]pyrrole-1,2-dicarboxylate (1421232-58-7)

Guidance literature:

Multi-step reaction with 11 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

10.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

11.1: palladium diacetate; triphenylphosphine; tributyl-amine; formic acid / N,N-dimethyl-formamide / 0.25 h / 65 °C

With 2,6-dimethylpyridine; formic acid; tributyl-amine; dihydrogen peroxide; palladium diacetate; 3,3-dimethyldioxirane; urea hydrogen peroxide adduct; silica gel; potassium hexamethylsilazane; sodium hydrogencarbonate; Dess-Martin periodane; hydrazine hydrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 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:

(2S,3aS,7aR)-1-benzyl 2-methyl 6-oxo-3,3a,7,7a-tetrahydro-1H-indole-1,2(2H,6H)-dicarboxylate (1421232-64-5) → (2S,8R,8aS)-1-benzyl 2-methyl 8-((tert-butyldimethylsilyl)oxy)-2,3,8,8a-tetrahydro-1H-oxepino[4,3-b]pyrrole-1,2-dicarboxylate (1421232-58-7)

Guidance literature:

Multi-step reaction with 10 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

9.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

10.1: palladium diacetate; triphenylphosphine; tributyl-amine; formic acid / N,N-dimethyl-formamide / 0.25 h / 65 °C

With 2,6-dimethylpyridine; formic acid; tributyl-amine; dihydrogen peroxide; palladium diacetate; 3,3-dimethyldioxirane; urea hydrogen peroxide adduct; silica gel; potassium hexamethylsilazane; sodium hydrogencarbonate; Dess-Martin periodane; hydrazine hydrate; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 2.1: |Wharton Fragmentation / 3.1: |Dess-Martin Oxidation / 6.1: |Wharton Fragmentation / 8.1: |Baeyer-Villiger Ketone Oxidation;

DOI:10.1002/anie.201207307

upstream raw materials:

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

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

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

(1aS,3aR,5S,6aR,6bS)-4-benzyl 5-methyl 2-oxohexahydro-1aH-oxireno[2,3-e]indole-4,5(2H)-dicarboxylate

Downstream raw materials:

(2S,8R,8aS)-1-((benzyloxy)carbonyl)-8-((tert-butyldimethylsilyl)oxy)-2,3,8,8a-tetrahydro-1H-oxepino[4,3-b]pyrrole-2-carboxylic acid

(2S,8R,8aS)-benzyl 8-((tert-butyldimethylsilyl)oxy)-2-((2S,8R,8aS)-8-((tert-butyldimethylsilyl)oxy)-2-(methoxycarbonyl)-2,3,8,8a-tetrahydro-1H-oxepino[4,3-b]pyrrole-1-carbonyl)-2,3,8,8a-tetrahydro-1H-oxepino[4,3-b]pyrrole-1-carboxylate

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