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A convenient and highly stereoselective method for synthesis of octahydropyrano[3,2-b]pyrrole derivatives

From National Research Council Canada

DOIResolve DOI: https://doi.org/10.1016/j.carres.2012.11.016
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Affiliation
  1. National Research Council of Canada. NRC Institute for Biological Sciences
FormatText, Article
SubjectBicyclic compounds; Pyranose; Pyrrole derivatives; Pyrrolidines; Reductive amination; Sodium triacetoxyborohydride; Stereoselective method; Stereoselective synthesis; Amines; Cyclization; Sodium; Stereochemistry; Stereoselectivity; Aromatic compounds; 1 benzyl 6,7 bis(benzyloxy) 5 [(benzyloxy)methyl] 2 methyl octahydropyrano(3,2 b)pyrrole; 1 hydroxyethyl 6,7 bis(benzyloxy) 5 [(benzyloxy)methyl] 2 methyl octahydropyrano(3,2 b)pyrrole; 3,7 anhydro 5,6,8 tri o benzyl 2 deoxy dextro manno octos 4 ulose; 4,8 anhydro 6,7,9 tri o benzyl 1,3 dideoxy dextro manno nono 2,5 diulose; 6,7 bis(benzyloxy) 5 [(benzyloxy)methyl] 1 (2 methoxy phenethyl)octahydropyrano(3,2 b)pyrrole; 6,7 bis(benzyloxy) 5 [(benzyloxy)methyl] 1 (4 fluorophenethyl)octahydropyrano(3,2 b)pyrrole; 6,7 bis(benzyloxy) 5 [(benzyloxy)methyl] 1 (4 tolyl) octahydropyrano(3,2 b)pyrrole; 6,7 bis(benzyloxy) 5 [(benzyloxy)methyl] 1 [2 (4 fluorophenyl)ethyl] 2 methyl octahydropyrano(3,2 b)pyrrole; 6,7 bis(benzyloxy) 5 [(benzyloxy)methyl] 1 butyl 2 methyl octahydropyrano(3,2 b)pyrrole; 6,7 bis(benzyloxy) 5 [(benzyloxy)methyl] 1 butyl octahydropyrano(3,2 b)pyrrole; 6,7 bis(benzyloxy) 5 [(benzyloxy)methyl] 1 hexyl 2 methyl octahydropyrano(3,2 b)pyrrole; 6,7 bis(benzyloxy) 5 [(benzyloxy)methyl] 1 hexyl octahydropyrano(3,2 b)pyrrole; 6,7 bis(benzyloxy) 5 [(benzyloxy)methyl] 1 hydroxyethyl octahydropyrano(3,2 b)pyrrole; 6,7 bis(benzyloxy) 5 [(benzyloxy)methyl] 1 octyl octahydropyrano(3,2 b)pyrrole; 6,7 bis(benzyloxy) 5 [(benzyloxy)methyl] 2 methyl 1 (4 methylphenyl)octahydropyrano[3,2 b)pyrrole; 6,7 bis(benzyloxy) 5 [(benzyloxy)methyl] 2 methyl 1 (o tolyl) octahydropyrano(3,2 b)pyrrole; 6,7 bis(benzyloxy) 5 [(benzyloxy)methyl] 2 methyl 1 octyl octahydropyrano(3,2 b)pyrrole; 6,7 bis(benzyloxy) 5 [(benzyloxy)methyl] 2 methyl 1 phenyl octahydropyrano(3,2 b)pyrrole; pyrrole derivative; unclassified drug; amination; biological activity; carbohydrate analysis; chemical interaction; column chromatography; cyclization; diastereoisomer; nuclear Overhauser effect; oxidation; ozonolysis; proton nuclear magnetic resonance; purification; stereochemistry; thin layer chromatography
Abstract
The octahydropyrano[3,2-b]pyrrole derivatives are synthesized by a double reductive amination from pyranose derivatives of nono-2,5-diuloses and octos-4-uloses and various amines. The cyclization proceeded smoothly in the presence of sodium triacetoxyborohydride to produce a series of novel fused N-heterobicyclic compounds with high stereoselectivity. © 2012 Elsevier Ltd. All rights reserved.
Publication date
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  • Carbohydrate Research 366 (2013): 55–62.
LanguageEnglish
Peer reviewedYes
NPARC number21269614
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Record identifier463aad72-0870-4444-b5f0-7aed8ee87d25
Record created2013-12-13
Record modified2020-04-22
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