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Expanding the Scope of Aminosugars: Synthesis of 2‐Amino Septanosyl Glycoconjugates Using Septanosyl Fluoride Donors
Author(s) -
Saha Jaideep,
Peczuh Mark W.
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201003721
Subject(s) - glycoconjugate , scope (computer science) , fluoride , chemistry , combinatorial chemistry , biochemistry , computer science , programming language , inorganic chemistry
A general strategy amenable to the strerocontrolled synthesis of complex, ring‐expanded analogues of natural aminoglycosides has been developed. Central to the method is the utilization of septanosyl fluorides as glycosyl donors in facile and selective glycosylation reactions. The septanosyl fluorides proved to be the best choice for the glycosylations because of their accessibility and the scope of aglycones that they could glycosylate. Moreover, a high degree of stereoselectivity was observed in the glycosylations, exclusively giving 1,2‐ trans ‐glycosides. 2‐Amino septanosyl fluorides were prepared from D ‐glucose, D ‐galactose, and D ‐mannose. Other routes to the septanosyl glyconjugates, especially with regard to alternate donor types, were systematically investigated. Since routes to the individual donor types were being explored, factors that exert a controlling influence on the acid‐mediated cyclization of 1,6‐hydroxy‐aldehydes were determined. The newly prepared 2‐amino septanosyl glycoconjugates illustrate the scope of the reaction and how it may be utilized for the preparation of other ring‐expanded analogues of glycosylated natural products.