(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

Base Information

• Chemical Name: (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
• CAS No.: 1421232-61-2
• Molecular Formula: C₃₉H₅₆N₂O₉Si₂
• Molecular Weight: 753.053
• Mol file: 1421232-61-2.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 13 articles about (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 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:

(2S,8R,8aS)-methyl 8-((tert-butyldimethylsilyl)oxy)-2,3,8,8a-tetrahydro-1H-oxepino[4,3-b]pyrrole-2-carboxylate (1421232-59-8) + (2S,8R,8aS)-1-((benzyloxy)carbonyl)-8-((tert-butyldimethylsilyl)oxy)-2,3,8,8a-tetrahydro-1H-oxepino[4,3-b]pyrrole-2-carboxylic acid (1421232-60-1) → (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 (1421232-61-2)

Guidance literature:

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1002/anie.201207307

Reference yield:

(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 (1421232-55-4) → (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 (1421232-61-2)

Guidance literature:

Multi-step reaction with 5 steps

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

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

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

4.1: palladium diacetate; triethylamine / dichloromethane / 0.08 h / 45 °C

4.2: 1.3 h / 45 °C

5.1: triethylamine; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride / dichloromethane / 24 h / 20 °C

With formic acid; tributyl-amine; palladium diacetate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; urea hydrogen peroxide adduct; potassium hexamethylsilazane; triethylamine; triphenylphosphine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: |Baeyer-Villiger Ketone Oxidation;

DOI:10.1002/anie.201207307

Reference yield:

(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)-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 (1421232-61-2)

Guidance literature:

Multi-step reaction with 3 steps

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

2.1: palladium diacetate; triethylamine / dichloromethane / 0.08 h / 45 °C

2.2: 1.3 h / 45 °C

3.1: triethylamine; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride / dichloromethane / 24 h / 20 °C

With formic acid; tributyl-amine; palladium diacetate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; triphenylphosphine; In dichloromethane; N,N-dimethyl-formamide;

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

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

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

Downstream raw materials:

acetylaranotin