202215-13-2

Basic information

• Product Name: (2R,3S,4S)-3,4-Bis-benzyloxy-2-vinyl-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS NO: 202215-13-2
• Molecular Weight: 409.525
• Mol File: 202215-13-2.mol

Chemical Properties

• CAS DataBase Reference: (2R,3S,4S)-3,4-Bis-benzyloxy-2-vinyl-pyrrolidine-1-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4S)-3,4-Bis-benzyloxy-2-vinyl-pyrrolidine-1-carboxylic acid tert-butyl ester(202215-13-2)
• EPA Substance Registry System: (2R,3S,4S)-3,4-Bis-benzyloxy-2-vinyl-pyrrolidine-1-carboxylic acid tert-butyl ester(202215-13-2)

Safety Data

• Hazardous Substances Data: 202215-13-2(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 202215-12-1 (2R,3S,4S)-(+)-N-tert-butoxycarbonyl-2-vinyl-3,4-dihydroxypyrrolidine 

Downstream Products

• 202215-17-6 (2R,3S,4S)-3,4-Bis-benzyloxy-2-vinyl-pyrrolidine 
• 202215-15-4 (1S,2S,8aR)-1,2-Bis-benzyloxy-2,3,6,8a-tetrahydro-1H-indolizin-5-one 
• 202215-14-3 1-((2R,3S,4S)-3,4-Bis-benzyloxy-2-vinyl-pyrrolidin-1-yl)-but-3-en-1-one 
• 125279-72-3 (1S,2S,8aR)-(-)-1,2-dihydroxyindolizidine 

Relevant articles and documents

Hydroxylated α-vinylpyrrolidines from sugar-derived 2,5-dihydrofurans. Synthesis of (1S,2S,8aR)-1,2-dihydroxyindolizidine by ring closing olefin methathesis

Sugar derived dihydrofurans carrying an amino function at the terminus of a two carbon branch undergo Hg(II)-promoted cyclization to give mercury substituted oxa-aza bicyclic compounds. Thiol promoted deoxymercuration results in cleavage of the tetrahyd rofuran ring and formation of hydroxylated 2-vinylpyrrolidines. These appear to be convenient precursors for the synthesis of indolizidines via ring-closing olefin metathesis. As an example the synthesis of a new lentiginosine epimer is reported.