1020084-75-6Relevant academic research and scientific papers
New building block for polyhydroxylated piperidine: Total synthesis of 1,6-dideoxynojirimycin
Rengasamy, Rajesh,Curtis-Long, Marcus J.,Woo, Duck Seo,Seong, Hun Jeong,Jeong, Ill-Yun,Ki, Hun Park
, p. 2898 - 2901 (2008/09/19)
(Chemical Equation Presented) (3R,4S)-3-Hydroxy-4-N-allyl-N-Boc-amino-1- pentene 10, an important precursor for the synthesis of polyhydroxylated piperidines, has been achieved as a single diastereomer without racemization via vinyl Grignard addition to N-Boc-N-allyl aminoaldehyde 9, which was derived from an enantiopure natural amino acid. Having forged a tetrahydropyridine ring scaffold 13 from 10 in 85% yield via RCM using Grubbs II catalyst, we were able to effect its stereodivergent dihydroxylation, via a common epoxide intermediate to yield a range of interesting hydroxylated piperidines, including ent-1,6-dideoxynojirimycin (ent-1,6-dDNJ) 1 (28% overall yield) and 5-amino-1,5,6-trideoxyaltrose 2 (29% over all yield) in excellent dr. To the best of our knowledge, our synthesis of ent-1,6-dDNJ 1 is the most expeditious to date.
