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Synthesis of D-(6R) - and D-(6S) -(6-2H1) glucose
Authors:Katsumi Kakinuma
Affiliation:Laboratory of Chemistry for Natural Products, Tokyo Institute of Technology, Midori-ku, Yokohama 227 Japan
Abstract:Chemical synthesis ofD-(6R)- and D(6S)-(6-2H1) glucose is described comprising (i) formation of 6-2H1)-3-o-benzyl-5,6-dideoxy-l, 2-0-isopropylidene-α-D-xylo-hex-5-ynofuranose from D-glucose; (ii) stereospecific reduction of the deuterated acetylene functionality to (E)- or (Z)-deuterated olefin; (iii) stereospecific cis-dihydroxylation of the deuterated olefin; and (iv) separation of stereoisomers based on the intrinsic chirality of D-glucose and subsequent deprotection.
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