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

Acta Crystallographica Section E: Crystallographic Communications

Mares, L.J.¹  Clarke, Z.²  Barnes, E.³  Prichard, K.L.⁴  Clegg, J.K.⁵ 

[1]Clinical Pharmacology, University of Newcastle, Callaghan, NSW 2308, Australia

[2]Discipline of Chemistry, University of Newcastle, Callaghan, NSW 2308, Australia

[3]Juniata College, Department of Chemistry, 1700 Moore Street, Huntingdon, Pennsylvania, PA16652-2196, USA

[4]Priority Research Centre for Chemical Biology &

[5]School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane St Lucia, QLD 4072, Australia

关键词: CRYSTAL STRUCTURE;    IMINOSUGAR;    D-GLUCOFURANOSE;    ELIMINATION;    SUBSTITUTION;    HYDROGEN BONDING;    C-H...[PI] INTERACTIONS;   

DOI  :  10.1107/S205698901800765X

学科分类：数学（综合）

来源: International Union of Crystallography

【 摘 要 】

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-iso­propyl­idene-5-O-methane­sulfonyl-6-O-tri­phenyl­methyl-α-d-gluco­furan­ose, C36H38O8S (3) [systematic name: 1-[(3aR,5R,6S,6aR)-6-benz­yloxy-2,2-di­methyl­tetra­hydro­furo[2,3-d][1,3]dioxol-5-yl)-2-(trit­yloxy)ethyl methane­sulfonate], a stable inter­mediate, and 5-azido-3-O-benzyl-5-de­oxy-1,2-O-iso­propyl­idene-6-O-tri­phenyl­methyl-β-l-ido­furan­ose, C35H35N3O5 (4) [systematic name: (3aR,5S,6S,6aR)-5-[1-azido-2-(trit­yloxy)eth­yl]-6-benz­yloxy-2,2-di­methyl­tetra­hydro­furo[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 mol­ecules in the crystals of both compounds were confirmed by resonant scattering. In the crystal of 3, neighbouring mol­ecules are linked by C—H⋯O hydrogen bonds, forming chains along the b-axis direction. The chains are linked by C—H⋯π inter­actions, forming layers parallel to the ab plane. In the crystal of 4, mol­ecules 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 inter­actions, forming a supra­molecular framework.

【 授权许可】

CC BY