Pinto, Brian Mario,Ghavami, Ahmad,Kumar, Nag Sharwan,Jensen, Henrik H.,Szczepina, Monica Gabriela,Johnston, Blair D.,Nasi, Ravindranath,Liu, Hui,Sadalapure, Kashinath
申请号：
AU2007219678
公开号：
AU2007219678B2
申请日:
2007.03.02
申请国别(地区):
AU
年份:
2012
代理人:
摘要：
Methods for synthesizing Salacinol, its stereoisomers, and analogues, homologuesand other derivatives thereof potentially useful as glycosidase inhibitorsare described. In some embodiments the compounds of the invention may have thegeneral formula (I) or (II). The synthetic schemes may comprise reacting a cyclicsulfate with a 5-membered ring sugar containing a heteroatom (X). The heteroatompreferably comprises sulfur, selenium, or nitrogen. The cyclic sulfate andring sugar reagents may be readily prepared from carbohydrate precursors, suchas D-glucose, L-glucose, D-xylose and L-xylose. The target compounds are preparedby opening of the cyclic sulfates by nucleophilic attack of the heteroatoms onthe 5-membered ring sugars. The resulting heterocyclic compounds have a stable,inner salt structure comprising a heteroatom cation and a sulfate anion. Thesynthetic schemes yield various stereoisomers of the target compounds in moderateto good yields with limited side-reactions. Chain-extended analogues of Salacinolare also described.
