294204-05-0Relevant academic research and scientific papers
All eight stereoisomeric D-glyconic-δ-lactams: Synthesis, conformational analysis, and evaluation as glycosidase inhibitors
Nishimura, Yoshio,Adachi, Hayamitsu,Satoh, Takahiko,Shitara, Eiki,Nakamura, Hikaru,Kojima, Fukiko,Takeuchi, Tomio
, p. 4871 - 4882 (2000)
An efficient and general synthetic route to all eight stereoisomeric D-glycono-δ-lactams has been developed. The strategy involves, as a key step, a stereodivergent δ-lactam formation with configurational retention or inversion at C-4 of a starting γ-lactone to lead to two epimers of δ-lactam from one parent γ-lactone. Conformations of eight glycono-δ-lactams were examined by X-ray crystallographic analysis and molecular modeling. Analyses of conformation and glycosidase-inhibition provide useful information for the design of new glycosidase inhibitors.
Combinatorial library approach to iminocyclitols with biological activity
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Page/Page column 12-13, (2008/06/13)
A method of synthesizing stereochemically defined iminocyclitol comprises replacing an intraring oxygen in a cyclic sugar by an intraring imine to form an iminocyclitol, wherein said iminocyclitol has a defined stereochemical configuration different from
Bicyclic diazasugars. Part 3: β-D-Mannose and 6-deoxy-β-L-gulose analogues
Berges, David A,Fan, Jianmei,Liu, Nannan,Kent Dalley
, p. 9915 - 9924 (2007/10/03)
A bicyclic analogue of β-D-mannopyranose with nitrogen atoms replacing the ring and glycosidic oxygen atoms has been prepared in a single step from 5-O-mesyl-D-mannofuranose by a process that likely involves double displacement and an epoxide intermediate. A similar but protected bicyclic analogue of 6-deoxy-β-L-gulopyranose has been prepared by an electrophilic cyclization reaction.
