Organic Letters
Letter
afforded the C-linked Gal-(1,6)-Gal disaccharide 23 in an α-
selective manner.
In conclusion, we have developed a direct approach for the
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synthesis of α-CH -linked (1,6)-disaccharide analogues from a
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Pastor, M.; Skrydstrup, T.; Jimen
002, 124, 14940−14951.
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stable C1-sp hybridized donor and the olefin acceptor. α-
2
(
Selective coupling was achieved by radical-based coupling of
4
the restricted C conformation of the donors and applied to
1
M. J. Am. Chem. Soc. 2007, 129, 15420−15421. (b) Watanabe, T.;
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the synthesis of CH -linked isomaltose analogue 16. This
2
methodology should be applicable to the synthesis of other C-
linked disaccharides.
2
008, 10, 4167−4170.
(7) Yang, G.; Schmieg, J.; Tsuji, M.; Franck, R. W. Angew. Chem., Int.
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ASSOCIATED CONTENT
Supporting Information
(8) Selected example of endo-C-glycoside analogues: (a) Shan, M.;
O’Doherty, G. A. Org. Lett. 2010, 12, 2986−2989. (b) Li, M.; Li, Y.;
Mrozowski, R. M.; Sandusky, Z. M.; Shan, M.; Song, X.; Wu, B.;
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Lannigan, D. A.; O’Doherty, G. A. Org. Lett. 2017, 19, 2410−2413.
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*
S
(9) Selected examples of the synthesis of (1,6)-C-disaccharides from
1
13
Detailed experimental procedures and H and C NMR
and HRMS data for new compounds (PDF)
noncarbohydrate based precursors: (a) Harding, M.; Nelson, A.
Chem. Commun. 2001, 695−696. (b) Narute, S. B.; Rout, J. K.;
Ramana, C. V. Chem. - Eur. J. 2013, 19, 15109−15114.
(
10) Selected examples of the synthesis of Glc-(1,6)-C-Glc
AUTHOR INFORMATION
■
*
*
disaccharides: (a) Goekjian, P. G.; Wu, T. C.; Kang, H. Y.; Kishi,
Y. J. Org. Chem. 1987, 52, 4823−4825. (b) Armstrong, R. W.;
Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743−7746. (c) Kobertz,
W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61,
1
894−1897. (d) Skrydstrup, T.; Mazea
Doisneau, G.; Riche, C.; Chiaroni, A.; Beau, J.-M. Chem. - Eur. J.
997, 3, 1342−1356. (e) Khan, N.; Cheng, X.; Mootoo, D. R. J. Am.
́
s, D.; Elmouchir, M.;
ORCID
1
Notes
Chem. Soc. 1999, 121, 4918−4919. (f) Spak, S. J.; Martin, O. R.
Tetrahedron 2000, 56, 217−224. (g) Dondoni, A.; Marra, A.; Mizuno,
M.; Giovannini, P. P. J. Org. Chem. 2002, 67, 4186−4199.
(h) Paterson, D. E.; Griffin, F. K.; Alcaraz, M.-L.; Taylor, R. J. K.
The authors declare no competing financial interest.
Eur. J. Org. Chem. 2002, 2002, 1323−1336. (i) Piper, J. L.; Postema,
M. H. D. J. Org. Chem. 2004, 69, 7395−7398. (j) Drouin, L.; Stanca-
Kaposta, E. C.; Saundh, P.; Fairbanks, A. J.; Kemper, S.; Claridge, T.
D. W.; Simons, J. P. Chem. - Eur. J. 2009, 15, 4057−4069.
(11) Koester, D. C.; Leibeling, M.; Neufeld, R.; Werz, D. B. Org.
Lett. 2010, 12, 3934−3937.
ACKNOWLEDGMENTS
■
This study was partially supported by PRIME (Grant Number
JP18gm5910018) and Platform Project for Supporting Drug
Discovery and Life Science Research (BINDS, Grant Number
JP18am0101091) from the Japan Agency for Medical Research
and Development, AMED, and the JSPS KAKENHI (Grant
Numbers 16H01167 and 18H04417 for Middle Molecular
Strategy and 18H02097) and JSPS A3 Foresight Program. We
also thank Mr. Arunpuksakul Nontapat (Chulalongkorn
University, Thailand) for his technical support.
(12) Representative C-linked disaccharide synthesis containing the
furanose structure or 2-deoxy sugar: (a) Tsuruta, O.; Yuasa, H.;
Kurono, S.; Hashimoto, H. Bioorg. Med. Chem. Lett. 1999, 9, 807−
8
10. (b) Lubin-Germain, N.; Baltaze, J.-P.; Coste, A.; Hallonet, A.;
Laurea
28.
13) Suzuki−Miyaura cross-coupling approach: Oroszova, B.;
Choutka, J.; Pohl, R.; Parkan, K. Chem. - Eur. J. 2015, 21, 7043−7047.
no, H.; Legrave, G.; Uziel, J.; Auge, J. Org. Lett. 2008, 10, 725−
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(
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Org. Lett. XXXX, XXX, XXX−XXX