Synthesis of iminoalditol and N-alkyl iminoalditol derivatives of ribopyranosides.
Iminoalditol analogs of ribopyranosides were prepared by reduction of a vinylogous urethane intermediate formed from methyl 2-C-(5-O-methanesulfonyl-beta-d-ribofuranosyl)acetate (1) by treatment with sodium azide in DMF at reflux. The N-alkylated analogs were synthesized either by N-alkylation of the corresponding parent iminoaldithol or, more efficiently, from the product of the reaction of 1 with various alkylamines. The latter process involves an S(N)2 substitution at C-5 by the amine followed by an intramolecular hetero-Michael reaction under basic conditions. The 'aglycon' of the iminoalditol was also modified through amidation and esterification.
Wu
An-Tai
AT
Department of Chemistry, National Changhua University of Education, Changhua 50058, Taiwan. antai@cc.ncue.edu.tw
Wu
Pey-Jiuann
PJ
Zou
Wei
W
Chir
Jiun-Ly
JL
Chang
Yuan-Chun
YC
Tsai
Shuan-Yi
SY
Guo
Chao-Qi
CQ
Chang
Wei-Shuan
WS
Hsieh
Yu-Chi
YC
D000475:Alkenes / Q000737:chemistry; D000478:Alkylation; D006027:Glycosides / Q000737:chemistry; D006586:Hexanes / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D009005:Monosaccharides / Q000737:chemistry; D012266:Ribose / Q000737:chemistry; D019810:Sodium Azide / Q000737:chemistry; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D014520:Urethane / Q000737:chemistry
D000475:Alkenes; D006027:Glycosides; D006586:Hexanes; D007202:Indicators and Reagents; D009005:Monosaccharides; D013402:Sugar Alcohols; D014520:Urethane; D012266:Ribose; D019810:Sodium Azide; C013658:propylene