203302-16-3

Basic information

• Product Name: 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-oxo-2,5-dihydro-thiophen-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• Synonyms: 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-oxo-2,5-dihydro-thiophen-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS NO: 203302-16-3
• Molecular Weight: 537.795
• Mol File: 203302-16-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-oxo-2,5-dihydro-thiophen-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-oxo-2,5-dihydro-thiophen-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester(203302-16-3)
• EPA Substance Registry System: 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-oxo-2,5-dihydro-thiophen-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester(203302-16-3)

Safety Data

• Hazardous Substances Data: 203302-16-3(Hazardous Substances Data)

Upstream product

• 164025-11-0 2-[(tert-butyldimethylsilyl)oxy]thiophene 
• 203301-82-0 (5R)-1-(tert-butoxycarbonyl)-2-methoxy-5-(tert-butyldiphenylsilanyloxymethyl)pyrrolidine 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 66673-40-3 (R)-5-hydroxymethylpyrrolidin-2-one 
• 24424-99-5 di-tert-butyl dicarbonate 

Relevant articles and documents

The Utility of Furan-, Pyrrole-, and Thiophene-Based 2-Silyloxy Dienes as Demonstrated by Modular Synthesis of Annonaceous Acetogenin Core Units and Their Pyrrolidine and Thiolane Analogues

We report a modular strategy for obtaining the core units of annonaceous acetogenins and their nitrogen and sulfur analogues, which generates great structural diversity. This synthesis is based on the application of a reiterative vinylogous addition protocol involving a unique triad of silyloxy diene modules, 2-[(tert-butyldimethylsilyl)oxy]furan (TBSOF), N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole (TBSOP), and 2-[(tert-butyldimethylsilyl)oxy]thiophene (TBSOT) and suitable heteroatom-stabilized carbenium ions. By combining TBSOF, TBSOP, and TBSOT nucleophilic synthons with certain tetrahydrofuran, pyrrolidine, and thiolane acceptors, the construction of varied, adjacently linked oligo-heterocyclic motifs related to the core segments of the annonaceous acetogenins is assured. At first, the reliability of the pivotal coupling maneuver was certified, by assembling a collection of 18 model constructs, covering all oxygen, nitrogen, and sulfur heteroatom combinations (i.e., compounds 7-9, 13-15, and 19-21). This uniformed protocol was then suited to forge advanced bis-tetrahydrofuran, bis-pyrrolidine, and bis-thiolane scaffolds encompassing the heterocyclic core portion of various binuclear annonaceous acetogenins and relatives. The utility of this synthesis was demonstrated by the preparation of a repertoire of eight isomeric bis-tetrahydrofuran units, 41-48, two bis-pyrrolidine units, 62 and 63, and four bis-thiolane units, 78-81.