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Synthesis of Spiro Carba‐Sugars by Ring‐Closing Metathesis
Author(s) -
GonzálezBello Concepción,
Castedo Luis,
Cañada Francisco Javier
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500655
Subject(s) - chemistry , ring closing metathesis , metathesis , stereochemistry , quinic acid , ring (chemistry) , cyclitol , ketone , olefin metathesis , organic chemistry , biochemistry , receptor , inositol , polymerization , polymer
Six conformationally restricted carba‐sugars have been synthesized by ring‐closing metathesis of a readily available diallyl keto derivative of (–)‐quinic acid. The rich functionality of the resulting spiro ketone was exploited for the diastereoselective synthesis of various spiro carba‐sugars: four of them polyhydroxylated and two aminopolyhydroxylated. The results of the testing of these compounds against various commercially available glycosidases (amyloglicosidase, α‐ and β‐galactosidase, α‐ and β‐ glucosidase, α‐mannosidase, trehalase and neuraminidase) are provided. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)