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DOI: 10.1055/s-2003-36815
Syntheses of Guanidinoglycosides with the Inventive use of Mitsunobu Conditions and 1,8-Diazabicyclo[5.4.0]undec-7-ene
Publikationsverlauf
Publikationsdatum:
22. Januar 2003 (online)

Abstract
A series of novel guanidinoglycosides was successfully synthesized. This was accomplished with the use of Mitsunobu conditions as a strategy to convert the glycopyranose anomeric hydroxy group to give the corresponding substituted masked guanidines in high yields. Subsequent deprotection and coupling with Fmoc protected β-amino acid, afforded a series of N,N′-substituted-methylisothioureas. Cleavage of Fmoc followed by concomitant cyclization was achieved with a catalytic amount of DBU to give the guanidinoglycosides.
Key words
guanidine - glycosides - Mitsunobu reaction - coupling - cyclization
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First and second authors contributed equally to this work.
12To further prove the existence of rotomers, Boc-protection of 2 was carried out using Boc2O and DMAP in CH2Cl2. Both 2a and 2b yielded only their respective α rotomers.