All eight stereoisomeric d-glyconic-δ-lactams: synthesis, conformational analysis, and evaluation as glycosidase inhibitors
Y Nishimura, H Adachi, T Satoh, E Shitara…
Index: Nishimura, Yoshio; Adachi, Hayamitsu; Satoh, Takahiko; Shitara, Eiki; Nakamura, Hikaru; Kojima, Fukiko; Takeuchi, Tomio Journal of Organic Chemistry, 2000 , vol. 65, # 16 p. 4871 - 4882
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Citation Number: 50
Abstract
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 ...
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