Article ID Journal Published Year Pages File Type
1346289 Tetrahedron: Asymmetry 2013 5 Pages PDF
Abstract

Highly functionalized polyhydroxylated dienoaldehyde, readily obtained from allyltin and d-glucose, served as a convenient precursor for a variety of configurationally different aza-bicyclic polyols. Such derivatives were deprotected and the activity of these free compounds against glycosidases was also tested.

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(4aR,5R,6S,7S,7aR)-5,6,7-Tris-benzyloxy-1-tosyl-2,4a,5,6,7,7a-hexahydro-1H-[1] pyrindineC36H37NO5S[α]Drt=+178.7 (c 1.0, CHCl3)Source of chirality: (E)-(2R,3S,4R)-2,3,4-Tris-benzyloxy-octa-5,7-dienalAbsolute configuration: (4aR,5R,6S,7S,7aR)

(3S,4R,4aS,5R,6S,7S,7aR)-5,6,7-Tris-benzyloxy-1,2,2-trimethyl-octahydro-[1] pyrindine-3,4-diolC36H37NO5S[α]Drt=+182.7 (c 1.0, CHCl3)Source of chirality: (E)-(2R,3S,4R)-2,3,4-Tris-benzyloxy-octa-5,7-dienalAbsolute configuration: (3S,4R,4aS,5R,6S,7S,7aR)

(3S,4S,4aS,5R,6S,7S,7aR)-5,6,7-Tris-benzyloxy-1-tosyl-octahydro-[1]pyrindine-3,4-diolC36H39NO7S[α]Drt=+172.9 (c 1.0, CHCl3)Source of chirality: (E)-(2R,3S,4R)-2,3,4-Tris-benzyloxy-octa-5,7-dienalAbsolute configuration: (3S,4S,4aS,5R,6S,7S,7aR)

(3R,4R,4aS,5R,6S,7S,7aR)-5,6,7-Tris-benzyloxy-1-tosyl-octahydro-[1]pyrindine-3,4-diolC36H39NO7S[α]Drt=+130.7 (c 1.0, CHCl3)Source of chirality: (E)-(2R,3S,4R)-2,3,4-Tris-benzyloxy-octa-5,7-dienalAbsolute configuration: (3R,4R,4aS,5R,6S,7S,7aR)

(3S,4R,4aS,5R,6S,7S,7aR)-Octahydro-[1]pyrindine-3,4,5,6,7-pentaol hexaacetateC20H27NO11[α]Drt=+26.9 (c 1.0, CHCl3)Source of chirality: (E)-(2R,3S,4R)-2,3,4-Tris-benzyloxy-octa-5,7-dienalAbsolute configuration: (3S,4R,4aS,5R,6S,7S,7aR)

(3S,4R,4aS,5R,6S,7S,7aR)-Octahydro-[1]pyridnine-3,4,5,6,7-pentaolC8H15NO5[α]Drt=+54.3 (c 1.0, CHCl3)Source of chirality: (E)-(2R,3S,4R)-2,3,4-Tris-benzyloxy-octa-5,7-dienalAbsolute configuration: (3S,4R,4aS,5R,6S,7S,7aR)

(3S,4S,4aS,5R,6S,7S,7aR)-Octahydro-[1]pyrindine-3,4,5,6,7-pentaol hexaacetateC20H27NO11[α]Drt=+21.7 (c 1.0, CHCl3)Source of chirality: (E)-(2R,3S,4R)-2,3,4-Tris-benzyloxy-octa-5,7-dienalAbsolute configuration: (3S,4S,4aS,5R,6S,7S,7aR)

(3S,4S,4aS,5R,6S,7S,7aR)-Octahydro-[1]pyrindine-3,4,5,6,7-pentaolC8H15NO6[α]Drt=-16.6 (c 1.0, CHCl3)Source of chirality: (E)-(2R,3S,4R)-2,3,4-Tris-benzyloxy-octa-5,7-dienalAbsolute configuration: (3S,4S,4aS,5R,6S,7S,7aR)

(3S,4S,5S,5aS,6R,7S,8S,8aR)-6,7,8-Tris-benzyloxy-9-oxa-1-aza-tricyclo [5.3.1.0∗2,6∗]undecane-3,4-diolC30H33NO6[α]Drt=-12.7 (c 1.0, CHCl3)Source of chirality: (1S,3S,4S,5R,7R,8S)-3,4,5-Tris-benzyloxy-11-oxa-1-aza-tricyclo[5.3.1.0∗2,6∗]undec-8-eneAbsolute configuration: (3S,4S,5S,5aS,6R,7S,8S,8aR)

(3S,4S,5S,5aR,6R,7S,8S,8aR)-6,7,8-Tris-benzyloxy-decahydro-cyclopenta[b]azepine-3,4,5-triolC30H35NO6[α]Drt=+3.0 (c 1.0, CHCl3)Source of chirality: (1S,3S,4S,5R,7R,8S)-3,4,5-Tris-benzyloxy-11-oxa-1-aza-tricyclo[5.3.1.0∗2,6∗]undec-8-eneAbsolute configuration: (3S,4S,5S,5aR,6R,7S,8S,8aR)

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