Phenyl 2-amino-N,6-O-dibenzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-β-d-glucopyranoside

In the crystal structure of the title compound, C27H27NO5S, the pyranose ring adopts a 4 C 1 chair conformation with puckering parameters Q = 0.639 (2) Å, θ = 174.11 (18) and ϕ = 256 (2)°. The presence of the 2,3-trans-oxazolidinone fixes the conformation of the pyranose ring. The phenyl group attached to the S atom and the benzyl group bonding to the N atom are each disordered over two positions with site occupancies of 0.624 (3):0.376 (3) and 0.526 (3):0.474 (3), respectively. An intermolecular O—H⋯O hydrogen bond is observed.

[1]  K. Benakli,et al.  Oxazolidinone protected 2-amino-2-deoxy-D-glucose derivatives as versatile intermediates in stereoselective oligosaccharide synthesis and the formation of alpha-linked glycosides. , 2001, Journal of the American Chemical Society.

[2]  S. Oscarson,et al.  Ethyl 2-acetamido-4,6-di-O-benzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-beta-D-glycopyranoside as a versatile GlcNAc donor. , 2005, Chemical communications.

[3]  Yukishige Ito,et al.  N-benzyl-2,3-oxazolidinone as a glycosyl donor for selective alpha-glycosylation and one-pot oligosaccharide synthesis involving 1,2-cis-glycosylation. , 2006, Journal of the American Chemical Society.

[4]  D. Cremer,et al.  General definition of ring puckering coordinates , 1975 .

[5]  Maria Cristina Burla,et al.  SIR2004: an improved tool for crystal structure determination and refinement , 2005 .

[6]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[7]  R. Blessing,et al.  An empirical correction for absorption anisotropy. , 1995, Acta crystallographica. Section A, Foundations of crystallography.

[8]  Louis J. Farrugia,et al.  ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI) , 1997 .

[9]  H. Flack,et al.  On enantiomorph‐polarity estimation , 1983 .

[10]  Li-he Zhang,et al.  Stereoselectivity investigation on glycosylation of oxazolidinone protected 2-amino-2-deoxy-D-glucose donors based on pre-activation protocol , 2008 .