01487nas a2200181   4500008004100000022001400041245019200055210006900247260010600316300001200422490000700434520063500441100002501076700002501101700002601126700002301152856013001175       2010                        eng d  a0957-416600aSynthesis of azepane and nojirimycin iminosugars: the sharpless asymmetric epoxidation of D-glucose-derived allyl alcohol and highly regioselective epoxide ring opening using sodium azide0 aSynthesis of azepane and nojirimycin iminosugars the sharpless a  aTHE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLANDbPERGAMON-ELSEVIER SCIENCE LTDcFEB  a163-1700 v213 a<p>The Sharp less asymmetric epoxidation of D-glucose-derived ally! alcohol 4 afforded alpha- and beta-epoxides 5a and 5b in high stereoselectivity. The epoxide ring opening in 5a/5b was studied with different nucleophilic azido reagents, under various reaction conditions, and was found to be highly regioselective to give the preferential formation of 6-azido diol 6a/6b over 5-azido-diol 7a/7b. The 6-azido diol 6a/6b and 5-azido dial 7a/7b thus obtained were converted to the corresponding seven- and six-membered iminosugar, namely, azepane 1a/1b and 1-deoxy-nojirimycin 2a/2b. (C) 2010 Elsevier Ltd. All rights reserved.</p>1 aJadhav, Vrushali, H.1 aBande, Omprakash, P.1 aPuranik, Vedavati, G.1 aDhavale, Dilip, D.  uhttps://library.ncl.res.in/content/synthesis-azepane-and-nojirimycin-iminosugars-sharpless-asymmetric-epoxidation-d-glucose-0