Synthesis of highly oxygenated decalins from sugar allyltins: an access to sulfur and phosphorus derivatives

A sugar allyltin derivative (with the d-gluco-configuration) was converted into d-xylo-dienoaldehyde and then into several bicyclic highly oxygenated compounds. The proposed methodology allows for a convenient synthesis of such derivatives containing heteroatoms other than oxygen. Molecular docking studies employing AutoDock 4.2 and AutoDock Vina were conducted in order to evaluate their activity as glycosidase inhibitors.

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(1R,2R,3S,4R,5R,6R,9S,10R)-1,2,3,4,6-Pentabenzyloxy-9-[(4′R)-2′,2′-dimethyl-1′,3′-dioxolane-4′-yl]bicyclo[4.4.0]dec-7,8-eneC50H54O7[α]D22=-11.2 (c 1, CHCl3)Source of chirality: chiral poolAbsolute configuration: (1R,2R,3S,4R,5R,6R,9S,10R,4′R)

(1S,4S,5R,6S,7R,8R,9S,10R,11S)-5,6,7,8-Tetrabenzyloxy-11-acetyloxy-13-oxatricyclo[8.3.0.04,9]tridec-2,3-eneC42H44O7[α]D22=+171.2 (c 1, CHCl3)Source of chirality: chiral poolAbsolute configuration: (1S,4S,5R,6S,7R,8R,9S,10R,11S)

(1R,2R,3S,4R,5R,9S,10R)-1,2,3,4-Tetrabenzyloxy-9-acetyloxymethylbicyclo[4.4.0]dec-6,7-eneC39H42O5[α]D22=+103.7 (c 1, CHCl3)Source of chirality: chiral poolAbsolute configuration: (1R,2R,3S,4R,5R,9S,10R)

(1R,2R,3S,4R,5R,9S,10R)-1,2,3,4-Tetrabenzyloxy-9-(benzyloxymethylene)bicyclo [4.4.0]dec-6,7-eneC46H48O5[α]D22=+71.0 (c 1, CHCl3)Source of chirality: chiral poolAbsolute configuration: (1R,2R,3S,4R,5R,9S,10R)

(1R,2R,3S,4R,5R,6R,9S,10R)-1,2,3,4-Tetrabenzyloxy-6-acetyloxy-9-(benzyloxymethyl)]bicyclo[4.4.0]dec-7,8-eneC48H50O7[α]D22=-12.5 (c 1, CHCl3)Source of chirality: chiral poolAbsolute configuration: (1R,2R,3S,4R,5R,6R,9S,10R)

(1R,2R,3S,4R,5R,6R,9S,10R)-[1,2,3,4-Tetrabenzyloxy-7-acetyloxy-9-(benzyloxymethylene)bicyclo[4.4.0]dec-5,6-eneC48H50O7[α]D22=-7.1 (c 1, CHCl3)Source of chirality: chiral poolAbsolute configuration: (1R,2R,3S,4R,5R,6R,9S,10R)

(1R,2R,3S,4R,5R,6S,7R,8S,9S,10R)-1,2,3,4-Tetrabenzyloxy-6,7,8-triacetyloxy-9-benzyloxymethylbicyclo[4.4.0]decaneC52H56O11[α]D22=-34.5 (c 1, CHCl3)Source of chirality: chiral poolAbsolute configuration: (1R,2R,3S,4R,5R,6S,7R,8S,9S,10R)

(1R,2R,3S,4R,7S,9S,10R)-1,2,3,4-Tetrabenzyloxy-9-benzyloxymethylbicyclo[4.4.0]-dec-5,6-en-7-yl 4-nitrobenzoateC53H51O9N[α]D22=+35.2 (c 1, CHCl3)Source of chirality: chiral poolAbsolute configuration: (1R,2R,3S,4R,7S,9S,10R)

(1R,2R,3S,4R,7S,9S,10R)-1,2,3,4-Tetrabenzyloxy-9-[(4′R)-2′,2′-dimethyl-1′,3′-dioxolan-4′-yl]bicyclo[4.4.0]-dec-5,6-en-7-yl 4-nitrobenzoateC50H51O10N[α]D22=+80.7 (c 1, CHCl3)Source of chirality: chiral poolAbsolute configuration: (1R,2R,3S,4R,7S,9S,10R,4′R)

(1R,2R,3S,4R,5R,6S,7S,9S,10R)-1,2,3,4-Tetrabenzyloxy-6-acetyloxy-7-thiocyano-9-[(4′R)-2′,2′-dimethyl-1′,3′-dioxolan-4′-ylo]bicyclo[4.4.0]decaneC46H51NO8S[α]D22=+16.6 (c 1, CHCl3)Source of chirality: chiral poolAbsolute configuration: (1R,2R,3S,4R,5R,6S,7S,9S,10R,4′R)

(1R,2R,3S,4R,5R,6S,7S,9S,10R)-1,2,3,4-Tetrabenzyloxy-6-thiocyano-7-acetyloxy-9-[(4′R)-2′,2′-dimethyl-1′,3′-dioxolan-4′-yl]bicyclo[4.4.0]decaneC46H51NO8S[α]D22=-1.4 (c 1, CHCl3)Source of chirality: chiral poolAbsolute configuration: (1R,2R,3S,4R,5R,6S,7S,9S,10R,4′R)

(1R,2R,3S,4R,5R,6S,7S,9S,10R)-1,2,3,4-Tetrabenzyloxy-6-acetyloxy-7-diphenylphosphoryl-9-[(4′R)-2′,2′-dimethyl-1′,3′-dioxolan-4′-yl]bicyclo[4.4.0]-decaneC57H61O9P[α]D22=-1.7 (c 1, CHCl3)Source of chirality: chiral poolAbsolute configuration: (1R,2R,3S,4R,5R,6S,7S,9S,10R,4′R)

(1R,2R,3S,4R,5R,6S,7S,9S,10R)-1,2,3,4-Tetrabenzyloxy-6-diphenylphosphoryl-7-acetyloxy-9-[(4′R)-2′,2′-dimethyl-1′,3′-dioxolan-4′-yl]bicyclo[4.4.0]-decaneC57H61O9P[α]D22=-1.4 (c 1, CHCl3)Source of chirality: chiral poolAbsolute configuration: (1R,2R,3S,4R,5R,6S,7S,9S,10R,4′R)

(1R,2R,3S,4R,5R,6S,7S,9S,10R)-1,2,3,4-Tetrabenzyloxy-6-hydroxy-7-sulfanyl-9-[(4′R)-2′,2′-dimethyl-1′,3′-dioxolan-4′-ylo]bicyclo[4.4.0]decaneC43H50O7S[α]D22=+20.5 (c 1, CHCl3)Source of chirality: chiral poolAbsolute configuration: (1R,2R,3S,4R,5R,6S,7S,9S,10R,4′R)

(1R,2R,3S,4R,5R,6S,7S,9S,10R)-1,2,3,4-Tetrabenzyloxy-6-sulfanyl-7-hydroxy-9-[4′R)-2′,2′-dimethyl-1′,3′-dioxolan-4′-ylo]bicyclo[4.4.0]decaneC43H50O7S[α]D29=+14.5 (c 1, CHCl3)Source of chirality: chiral poolAbsolute configuration: (1R,2R,3S,4R,5R,6S,7S,9S,10R,4′R)