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The effect of different leaving groups on the substitution versus elimination outcomes with C-5 d-glucose derivatives was investigated. The stereochemical configurations of 3- O -benzyl-1,2- O -iso-propyl-idene-5- O -methane-sulfonyl-6- O -tri-phenyl-methyl-α-d-gluco-furan-ose, C 36 H 38 O 8 S ( 3 ) [systematic name: 1-[(3a R ,5 R ,6 S ,6a R )-6-benz-yloxy-2,2-di-methyl-tetra-hydro-furo[2,3- d ][1,3]dioxol-5-yl)-2-(trit-yloxy)ethyl methane-sulfonate], a stable inter-mediate, and 5-azido-3- O -benzyl-5-de-oxy-1,2- O -iso-propyl-idene-6- O -tri-phenyl-methyl-β-l-ido-furan-ose, C 35 H 35 N 3 O 5 ( 4 ) [systematic name: (3a R ,5 S ,6 S ,6a R )-5-[1-azido-2-(trit-yloxy)eth-yl]-6-benz-yloxy-2,2-di-methyl-tetra-hydro-furo[2,3- d ][1,3]dioxole], a substitution product, were examined and the inversion of configuration for the azido group on C-5 in 4 was confirmed. The absolute structures of the mol-ecules in the crystals of both compounds were confirmed by resonant scattering. In the crystal of 3 , neighbouring mol-ecules are linked by C-H⋯O hydrogen bonds, forming chains along the b -axis direction. The chains are linked by C-H⋯π inter-actions, forming layers parallel to the ab plane. In the crystal of 4 , mol-ecules are also linked by C-H⋯O hydrogen bonds, forming this time helices along the a -axis direction. The helices are linked by a number of C-H⋯π inter-actions, forming a supra-molecular framework.

acta crystallographica. section e, crystallographic communications

The crystal structures of 3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-6-O-triphenylmethyl-α-<scp>D</scp>-glucofuranose and its azide displacement product

The crystal structures of 3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-6-O-triphenylmethyl-α-D-glucofuranose and its azide displacement product