609355-98-8Relevant articles and documents
Concise and practical route to tri- and tetra-hydroxy seven-membered iminocyclitols as glycosidase inhibitors from d-(+)-glucurono-γ-lactone
Kalamkar, Navnath B.,Kasture, Vijay M.,Chavan, Sanjay T.,Sabharwal, Sushma G.,Dhavale, Dilip D.
experimental part, p. 8522 - 8526 (2010/11/18)
An efficient and short total synthesis of tetrahydroxy-1c and trihydroxy-azepane 1d is reported in 72% and 57% overall yields, respectively, from d-(+)-glucurono-γ-lactone. Thus, d-glucuronolactone 2 on acetonide protection, DIBAL-H reduction and one-pot intermolecular reductive amination followed by -NCbz protection afforded 6-(N-benzyl-N-benzyloxycarbonyl) amino-6-deoxy-1,2-O-isopropylidene-α-d-gluco-1,4-furanose 5a. 1,2-Acetonide hydrolysis in 5a and Pd-mediated intramolecular reductive aminocyclization afforded tetrahydroxyazepane 1c. An analogous pathway with 5-deoxy-1,2-O-isopropylidene-α-d-glucurono-6,3-lactone 3b gave trihydroxy-azepane 1d. Glycosidase inhibitory activity of 1c/1d was studied and 1d was found to be potent inhibitor of α-mannosidase and β-galactosidase.
An expeditious synthesis of a (3S,4S,5R)-trihydroxyazepane
Dhavale, Dilip D.,Chaudhari, Vinod D.,Tilekar, Jayant N.
, p. 7321 - 7323 (2007/10/03)
A practical approach for the synthesis of the (2S,3S,4R)-trihydroxyazepane 1d has been reported. Starting from α-D-xylo-pentodialdose, readily available from D-glucose, the sequence involves Wittig olefination and reductive amination as key steps.
