126550-74-1

Upstream product

• 100-39-0 benzyl bromide 
• 138528-06-0 (2S,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-hydroxymethylpyrrolidine 
• 126550-75-2 (2S,5S)-1-t-butoxycarbonyl-(2,5)-bis(hydroxymethyl)pyrrolidine 
• 14618-80-5 (R)-benzyl glycidol 
• 155418-40-9 (2S)-1-(benzyloxy)hex-5-en-2-ol 
• 126550-70-7 (R)-1-Benzyloxymethyl-pent-4-enylamine 
• 175229-12-6 (R)-3-benzyloxy-2-(tert-butoxycarbonylamino)propyl phenyl sulfone 
• 116611-44-0 ((R)-2-benzenesulfonyl-1-hydroxymethyl-ethyl)carbamic acid tert-butyl ester 
• 253776-34-0 (2S)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate) 
• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 
• 253776-40-8 (2R,5S)-3-Benzenesulfonyl-2,5-bis-benzyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 126550-73-0 N-Boc-2-(S)-benzoyloxymethyl-5-(S)-benzyloxy methylpyrrolidine 
• 126550-69-4 2-((R)-1-Benzyloxymethyl-pent-4-enyl)-isoindole-1,3-dione 
• 126550-72-9 (2S,5S)-2-benzyloxymethyl-5-benzoyloxymethylpyrrolidine 

Downstream Products

• 188401-92-5 (2S,5S)-2,5-bis(benzyloxymethyl)pyrrolidine 

Relevant academic research and scientific papers

A novel method for chirospecific synthesis of 2,5-disubstituted pyrrolidines

One-pot ring formation using (R)-1 or (S)-1 as a nucleophile and homochiral glycidyl triflate (R)-2 or (S)-2 as an electrophile provides a pivotal intermediate 4 which can be transformed into a 2,5-disubstituted pyrrolidine with any desired stereochemistr

A Versatile Method for the Facile Synthesis of Enantiopure trans-and cis-2,5-Disubstituted Pyrrolidines

Treatment of (2S)-1-O-benzylglycerol-2,3-bistriflate (2) with the trilithiated species of chiral building blocks 5-7 provided 2,3,5-trisubstituted pyrrolidines that were subjected to reductive desulfonylation to give trans-2,5-disubstituted pyrrolidines 11-13, respectively. The same reaction sequence with the (2R)-bistriflate 4 and trilithiated 5 afforded the eis isomer 19. This two-step synthetic mehodology can furnish any one of the four possible diastereomers of enantiopure 2,5-disubstituted pyrrolidines in 60-72% overall yields.

Versatile synthesis of enantiomerically pure trans-2,5-disubstituted pyrrolidines

Enantiomerically pure trans-(2S,5S)-2,5-disubstituted pyrrolidine was synthesized starting from the versatile chiral synthon (R)-(8) and chiral 2,3-O-isopropylideneglycerol triflate (S)-(9).

CONCISE SYNTHESIS OF C2-SYMMETRIC TRANS-2,5-DIOXYMETHYLPYRROLIDINE DERIVATIVES BY NOVEL CYCLIZATION

Treatment of (S)-1-benzyloxy-2-benzoylaminohex-5-ene with iodine in aqueous acetonitrile furnished (2S,5S)-5-benzoyloxymethyl-2-bemzyloxymethylpyrrolidine stereoselectively in a single step.The product was converted into C2-symmetric (2S,5S)-2,5-dioxymethylpyrrolidines potentially utilizable as chiral auxiliaries and (2S,5S)-(-)-pyrrolidine-2,5-dicarboxylic acid isolated from marine alga Schizymenia dubyi.