Kimura, M. Sekine, D. Takahashi, K. Toshima, Angew. Chem. Int. Ed. 2013,
52, 12131-12134.
NBS, 1-dihydroxyboryl benzyl S-glucosides served as glycosyl
donors for O-glycosylation. It was found that the boronic acid moiety
was essential in the glycosylation for product formation and good
anomeric ratio. After optimization of the glycosylation step, some
simple 1,2-cis-O-glycosides could be prepared with good to perfect
anomeric ratio. Although there is room to improve the glycosylation
yield and broaden the substrate scope, the preliminary model
reactions suggested that glycosyl aryl boronic acids could be used for
stereoselective glycosylation.
[6]
[7]
(a) G. Chen, X. Gu, L. Chen, X. Wang, Y.-L. Chen, J. Shen, W. Zeng,
Protein and Peptide Letters, accepted for publication; (b) Y.-L. Chen et al,
unpublished results.
1
2
3
4
5
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7
8
9
Frequently, such activation is not good enough for the generation of a
C-1 leaving group at low temperature, even in the presence of
intracyclic oxygen. With NBS, glycosylation with 1-PhS glycosides
o
proceeds at 25 C. See: (a) K. C. Nicolaou, S. P. Seitz, D. P. Papahatjis, J.
Am. Chem. Soc. 1983, 105, 2430-2434; and this reaction was very slow at
low temperature according to our experiments. Also, the stereochemistry
outcome is not satisfying for most of the examples. The activation of S-
glycosides with NBS is more often associated with an acid, see for
example: (b) Z.-H. Qin, H. Li, M.-S. Cai, Z.-J. Li, Carbohydr. Res. 2002,
337, 31-36; (c) M. Sasaki, K. Tachibana, H. Nakanishi, Tetrahedron Lett.
1991, 32, 6873-6876.
Acknowledgments
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This work was supported by the National Natural Science
[8]
An ate complex may enhance the nucleophilicity of the oxygen: see for
example: (a) S. E. Denmark, G. L. Beutner, Angew. Chem. Int. Ed. 2008, 47,
1560-1638. In carbohydrate chemistry, particular boronates and borinates
were also found to enhance the reactivity of glycosyl acceptors. This was
largely demonstrated by Aoyama et al: (b) K. Oshima, T. Yamauchi, M.
Shimomura, S. Miyauchi, Y. Aoyama, Bull. Chem. Soc. Jpn. 2002, 75,
1319-1324; (c) K. Oshima, Y. Aoyama, J. Am. Chem. Soc. 1999, 121,
2315-2316; (d) K. Oshima, E.-i. Kitazono, Y. Aoyama, Tetrahedron Lett.
1997, 38, 5001-5004; and by Taylor et al: (e) C. A. McClary, M. S. Taylor,
Carbohydr. Res. 2013, 381, 112-122; (f) E. Dimitrijevic, M. S. Taylor,
Chem. Sci. 2013, 4, 3298-3303; (g) D. Lee, C. L. Williamson, L. Chan, M.
S. Taylor, J. Am. Chem. Soc. 2012, 134, 8260-8267; (h) D. Lee, M. S.
Taylor, J. Am. Chem. Soc. 2011, 133, 3724-3727; (i) C. Gouliaras, D. Lee,
L. Chan, M. S. Taylor, J. Am. Chem. Soc. 2011, 133, 13926-13929; (j) L.
Chan, M. S. Taylor, Org. Lett. 2011, 13, 3090-3093; and by Madsen et al:
(k) T. H. Fenger, R. Madsen, Eur. J. Org. Chem. 2013, 26, 5923-5933.
Foundation of China (81102306) and National Science
&
Technology Major Project “Key New Drug Creation and
Manufacturing Program”, China (2012ZX09301001).
References and notes
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(a) Glycoscience (Eds.: B. Fraser-Reid, K. Tatsuta, J. Thiem), Springer
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Org. Lett. 2013, 15, 2566-2569.
[9]
Both anomers of 15 were prepared from compound 8 according to literature
procedures. For DMF assisted 1,2-cis-glycosylation, see S.-R. Lu, Y.-H. Lai,
J.-H. Chen, C.-Y. Liu, K.-K. T. Mong, Angew. Chem. Int. Ed. 2011, 50,
7315-7320; For experimental details, see supporting information.
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[11] Addition of TfOH could facilitate the departure of the sulphide leaving
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For related concepts: a) R. B. Woodward, E. Logusch, K. P. Nambiar, K.
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C. H. Chen, et al, J. Am. Chem. Soc. 1981, 103, 3215-3217; b) S. Hanessian,
C. Bacquet, N. Lehong, Carbohydr. Res. 1980, 80, C17-C22; c) M. E.
Behrendt, R. R. Schmidt, Tetrahedron Lett. 1993, 34, 6733-6736; K. L. M.
Hoang, Y. Bai, X. Ge, X.-W. Liu, J. Org. Chem. 2013, 78, 5196-5204.
Supplementary Material
(a) Y. Geng, A. Kumar, H. M. Faidallah, H. A. Albar, I. A. Mhkalid, R. R.
Schmidt, Angew. Chem. Int. Ed. 2013, 52, 10089–10092; (b) A. Kumar, V.
Kumar, R. T. Dere, R. R. Schmidt, Org. Lett. 2011, 13, 3612-3615; c) T.
Experimental details and copies of NMR spectra.
4