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

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Chemical Name:(2S,8R,8aS)-1-((benzyloxy)carbonyl)-8-((tert-butyldimethylsilyl)oxy)-2,3,8,8a-tetrahydro-1H-oxepino[4,3-b]pyrrole-2-carboxylic acid
CAS No.:1421232-60-1
Molecular Formula:C₂₃H₃₁NO₆Si
Molecular Weight:445.588
Hs Code.:

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

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

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

There total 12 articles about (2S,8R,8aS)-1-((benzyloxy)carbonyl)-8-((tert-butyldimethylsilyl)oxy)-2,3,8,8a-tetrahydro-1H-oxepino[4,3-b]pyrrole-2-carboxylic acid 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:

: 1421232-58-7
(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

: 1421232-60-1
(2S,8R,8aS)-1-((benzyloxy)carbonyl)-8-((tert-butyldimethylsilyl)oxy)-2,3,8,8a-tetrahydro-1H-oxepino[4,3-b]pyrrole-2-carboxylic acid

Guidance literature:: With water; potassium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 1.5h;
DOI:10.1002/anie.201207307

Reference yield:

: 1421232-57-6
(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

: 1421232-60-1
(2S,8R,8aS)-1-((benzyloxy)carbonyl)-8-((tert-butyldimethylsilyl)oxy)-2,3,8,8a-tetrahydro-1H-oxepino[4,3-b]pyrrole-2-carboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

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

2: potassium hydroxide; water / methanol; tetrahydrofuran / 1.5 h / 20 °C

With formic acid; tributyl-amine; water; palladium diacetate; triphenylphosphine; potassium hydroxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
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

: 1421232-60-1
(2S,8R,8aS)-1-((benzyloxy)carbonyl)-8-((tert-butyldimethylsilyl)oxy)-2,3,8,8a-tetrahydro-1H-oxepino[4,3-b]pyrrole-2-carboxylic acid

Guidance literature:: Multi-step reaction with 12 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

12.1: potassium hydroxide; water / methanol; tetrahydrofuran / 1.5 h / 20 °C

With 2,6-dimethylpyridine; formic acid; tributyl-amine; water; 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; potassium hydroxide; 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