213271-96-6Relevant academic research and scientific papers
Synthesis of N-alkoxytrihydroxypiperidine analogs of allopyranose
Sun, Lihong,Li, Pan,Landry, Donald W.,Zhao, Kang
, p. 1547 - 1550 (1996)
Tandem reductive cyclization of O-alkyl oximes provides an efficient method for the preparation of N-alkoxytrihydroxypiperidine analogs of allopyranose as potential glycosidase inhibitors.
N-alkoxy analogues of 3,4,5-trihydroxypiperidine
Sun, Lihong,Li, Pan,Amankulor, Nduka,Tang, Weiping,Landry, Donald W.,Zhao, Kang
, p. 6472 - 6475 (2007/10/03)
Two practical procedures are described for the synthesis of the N- alkoxy analogues of 3,4,5-trihydroxypiperidine. The key feature of these methods is the intramolecular N-cyclization of hydroxylamine derivatives which are readily obtained from the reduction of the corresponding oximes. One method is to reductively hydroxyaminate an aldehyde group in the presence of a primary tosylated alcohol which is subsequently cyclized in situ upon neutralization. The intramolecular Mitsunobu coupling of a hydroxylamine with a primary alcohol proved useful for the preparation of compounds which contained the trans diol structure.
