203301-82-0

Basic information

• Product Name: (5R)-1-(tert-butoxycarbonyl)-2-methoxy-5-(tert-butyldiphenylsilanyloxymethyl)pyrrolidine
• Synonyms: (5R)-1-(tert-butoxycarbonyl)-2-methoxy-5-(tert-butyldiphenylsilanyloxymethyl)pyrrolidine
• CAS NO: 203301-82-0
• Molecular Weight: 469.696
• Mol File: 203301-82-0.mol

Chemical Properties

• CAS DataBase Reference: (5R)-1-(tert-butoxycarbonyl)-2-methoxy-5-(tert-butyldiphenylsilanyloxymethyl)pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (5R)-1-(tert-butoxycarbonyl)-2-methoxy-5-(tert-butyldiphenylsilanyloxymethyl)pyrrolidine(203301-82-0)
• EPA Substance Registry System: (5R)-1-(tert-butoxycarbonyl)-2-methoxy-5-(tert-butyldiphenylsilanyloxymethyl)pyrrolidine(203301-82-0)

Safety Data

• Hazardous Substances Data: 203301-82-0(Hazardous Substances Data)

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 66673-40-3 (R)-5-hydroxymethylpyrrolidin-2-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 149-73-5 trimethyl orthoformate 
• 138629-30-8 (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester 
• 138629-44-4 (R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-2-one 

Downstream Products

• 266345-85-1 5-(tert-butyl-diphenyl-silanyloxymethyl)-5'-oxo-[2,2']bipyrrolidinyl-1,1'-dicarboxylic acid di-tert-butyl ester 
• 266345-28-2 5-(tert-butyl-diphenyl-silanyloxymethyl)-5'-oxo-[2,2']bipyrrolidinyl-1,1'-dicarboxylic acid di-tert-butyl ester 
• 203301-98-8 (2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((R)-5-oxo-tetrahydro-furan-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 203302-16-3 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-oxo-2,5-dihydro-thiophen-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 266345-27-1 5-(tert-butyl-diphenyl-silanyloxymethyl)-5'-oxo-2,3,4,5,2',5'-hexahydro-[2,2']bipyrrolyl-1,1'-dicarboxylic acid di-tert-butyl ester 
• 266345-83-9 5-(tert-butyl-diphenyl-silanyloxymethyl)-5'-oxo-2,3,4,5,2',5'-hexahydro-[2,2']bipyrrolyl-1,1'-dicarboxylic acid di-tert-butyl ester 
• 203302-14-1 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-oxo-2,5-dihydro-furan-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Diastereoselective synthesis of 4,5′-bis-proline compounds via reductive dimerization of N-acyloxyiminium ions

A short, practical synthesis of novel, unsymmetrical 4,5′-bis-proline compounds has been achieved, highlighted by the application of an unprecedented samarium diiodide-driven regio- and diastereocontrolled reductive dimerization of N-acyloxyiminium ions generated from readily available 2-methoxy-5- silyloxymethyl-N-Boc pyrrolidines. The title proline dimers proved to be pertinent metal-free catalysts in aldol and Mannich reactions.

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.