01437nas a2200205   4500008004100000022001400041245014800055210006900203260011000272300001400382490000600396520057500402100002300977700002101000700002501021700001501046700002601061700002201087856012201109       2005                        eng d  a1477-052000aAziridine carboxylate from D-glucose: synthesis of polyhydroxylated piperidine, pyrrolidine alkaloids and study of their glycosidase inhibition0 aAziridine carboxylate from Dglucose synthesis of polyhydroxylate  aTHOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLANDbROYAL SOC CHEMISTRYcOCT  a3720-37260 v33 a<p>The D-glucose derived aziridine carboxylate 5 was obtained from (E)-ethyl-6-bromo-1,2-O-isopropylidene-3-O-benzyl-5-deoxy-alpha-D-xylo-5 -eno-heptofuranuronate 4 through conjugate addition of benzylamine and in situ intramolecular nucleophilic expulsion of bromine. The regioselective aziridine ring-opening, using water as a nucleophile, resulted in the alpha-hydroxy-beta-aminoester 6, which was exploited in the synthesis of six and five membered azasugars 1b/1c and 2b/2c, respectively The glycosidase inhibitory activity of the title compounds was evaluated.</p>1 aDhavale, Dilip, D.1 aKumar, K., S. A.1 aChaudhari, Vinod, D.1 aSharma, T.1 aSabharwal, Sushma, G.1 aPrakashaReddy, J.  uhttp://library.ncl.res.in/content/aziridine-carboxylate-d-glucose-synthesis-polyhydroxylated-piperidine-pyrrolidine-002334nas a2200229   4500008004100000022001400041245017300055210006900228260007100297300001400368490000700382520140600389100002101795700002601816700002301842700002201865700002301887700002601910700002601936700002301962856011901985       2012                        eng d  a0022-326300aAlpha-geminal dihydroxymethyl piperidine and pyrrolidine iminosugars: synthesis, conformational analysis, glycosidase inhibitory activity, and molecular docking studies0 aAlphageminal dihydroxymethyl piperidine and pyrrolidine iminosug  a1155 16TH ST, NW, WASHINGTON, DC 20036 USAbAMER CHEMICAL SOCcSEP  a7873-78820 v773 a<p>The Jocic-Reeve and Corey-Link type reaction of dichloromethyllithium with suitably protected 5-keto-hexofuranoses followed by treatment with sodium azide and sodium borohydride reduction gave 5-azido-5-hydroxylmethyl substituted hexofuranoses 7a-c with required geminal dihydroxymethyl group. Removal of protecting groups and converting the C-1 anomeric carbon into free hemiacetal followed by intramolecular reductive aminocyclization with in situ generated C5-amino functionality afforded corresponding 5C-dihydroxymethyl piperidine iminosugars 2a-c. Alternatively, removal of protecting groups in 7b and 7c and chopping of C1-anomeric carbon gave C2-aldehyde that on intramolecular reductive aminocyclization with CS-amino gave 4C-dihydroxyrnethyl pyrrolidine iminosugars 1b and 1c, respectively. On the basis of the H-1 NMR studies, the conformations of 2a/2b were assigned as C-4(1) and that of 2c as C-1(4). The glycosidase inhibitory activities of all five iminosugars were studied with various glycosidase enzymes and compared with natural o-g/uco-l-deoxynojirimycin (DNJ). All the five compounds were found to be potent inhibitors of rice alpha-glucosidase with K-i and IC50 values in the nanomolar concentration range. Iminosugars 2b and 1b were found to be more potent inhibitors than their parent iminosugar. These results were substantiated by in silico molecular docking studies.</p>1 aPawar, Nitin, J.1 aParihar, Vijay, Singh1 aChavan, Sanjay, T.1 aJoshi, Rakesh, S.1 aJoshi, Pranaya, V.1 aSabharwal, Sushma, G.1 aPuranik, Vedavati, G.1 aDhavale, Dilip, D.  uhttp://library.ncl.res.in/content/alpha-geminal-dihydroxymethyl-piperidine-and-pyrrolidine-iminosugars-synthesis-0