Convergent Total Syntheses of Oligosaccharides by One-Pot Sequential Stereoselective Glycosylations

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A convergent total synthesis of F1α antigen, a member of the tumor-associated <I>O</I>-linked mucin glycosyl amino acid, was tried by one-pot sequential glycosylation. Highly α-selective glycosylation of amino acid <B>7</B> with thioglycoside <B>6</B> was successfully carried out by combining trityl trifluoromethanesulfonate (TrOTf) and <I>N</I>-iodosuccimide (NIS) which gave glycosyl amino acid <B>21</B> in high yield (97%, α/β = 83⁄17). Next, the glycosylation of thioglycoside <B>4</B> with galactosyl phenyl carbonate <B>2</B> or fluoride <B>3</B> was tried by the promotion of trityl tetrakis(pentafluorophenyl)borate [TrB(C<SUB>6</SUB>F<SUB>5</SUB>)<SUB>4</SUB>] or trifluoromethanesulfonic acid (TfOH); protected F1α <B>25</B> was afforded in 80 or 89% overall yield, respectively, by the further addition of glycosyl amino acid <B>5</B> and NIS. The desired trisaccharide was obtained in high yield after removal of the protecting groups. Next, a convergent total synthesis of branched hepta-β-glucoside <B>30</B> having phytoalexin-elicitor activity was efficiently performed by way of two one-pot sequential glycosylation reactions: that is, trisaccharide <B>34</B> was synthesized in high yield by TfOH-catalyzed one-pot glycosylation using three given monosaccharides (<B>31</B>, <B>35</B>, and <B>36</B>) as shown in Scheme 12 and by subsequent selective deprotection of 6′-<I>O</I>-TBDPS group. The second one-pot glycosylation of trisaccharide <B>34</B> with three monosaccharides (<B>31</B>, <B>32</B>, and <B>33d</B>) also proceeded smoothly to afford heptaglucoside <B>43</B> stereoselectively in 48% total yield based on monosaccharide <B>32</B>. Phytoalexin-elicitor active branched hepta-β-glucoside <B>30</B> was afforded by the sequential deprotection.

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  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 76(9), 1829-1848, 2003-09-15

    公益社団法人 日本化学会

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