Formation of carbon – oxygen single bonds is one of the most fundamental and most frequently used important reaction in synthetic chemistry of carbohydrates. The choice of efficient protective group in the synthesis of a complex molecules is often main stage.^1,2 The p-nitrobenzyl protecting group has seen use in the protection of alcohols, thiols, amines and carboxylic acids.³  p-Nitrobenzyl glycosides are stable building blocks used in synthesis of oligosaccharides or complex glycoconjugates which exhibiting various biological activity. p-Nitrobenzyl groups can be reduced to the amino group which can be used as spacer in the synthesis of glycoconjugates.

In this communication we report the novel method protection of hydroxyl functionality group in the sugars and isoflavonoids using p-nitrobenzyl thiocarbamates as donors. These compounds are readily obtained from p-nitrobenzyl alcohol in the reaction with commercially available N-allyl isothiocyanate⁴, N-benzyl isothiocyanate and N-phenyl isothiocyanate. We obtained p-nitrobenzylglycoside with high α-stereoselectivity and p-nitrobenzyl derivative of isoflavonoid with good yield. In summary both this products can be used in the synthesis of glycoconjugates.

Acknowledgement

Research studies part-financed by the European Union within the European Regional Development Fund (POIG. 01.01.02-14-102/09).

References

¹ Green, T.; Wuts, P. Protective Groups in Organic Synthesis, 2^nd ed.: John Wiley and Sons: New York, 1997. ² Levy, D. E.; Fϋgelli, P. The Organic Chemistry of Sugars, Taylor Francis Group LLC: New York, 2006. ³ Jarowicki, K.; Kocienski, P. J. Chem. Soc., Perkin Trans. 1, 2000, 2495. ⁴ Kasprzycka, A.; Szeja, W. Polish J. Chem. 2005, 79, 329-333.

• Legal notice:
  

  Copyright (c) Pielaszek Research, all rights reserved.
  The above materials, including auxiliary resources, are subject to Publisher's copyright and the Author(s) intellectual rights. Without limiting Author(s) rights under respective Copyright Transfer Agreement, no part of the above documents may be reproduced without the express written permission of Pielaszek Research, the Publisher. Express permission from the Author(s) is required to use the above materials for academic purposes, such as lectures or scientific presentations.
  In every case, proper references including Author(s) name(s) and URL of this webpage: https://science24.com/paper/26751 must be provided.

1. Synthesis of 1’-(saccharide)substituted 28-O-(1’H-[1’,2’,3’]triazolyl-4’-methyl) derivatives of protoescigenin
2. Hexenoses in design of glycoconjugates – from chemistry to function
3. Fucosyl derivatives in the synthesis of uridine glycoconjugates - potential glycosyltransferase inhibitors
4. Unsaturated saccharides as a useful chiral synthons and their application in synthesis  of polyphenol glycoconjugates - potential antiproliferative agents
5. Fungicidal activity of thionocarbamates derivatives of alcohols
6. Isolation and application of β-galactosidases  in the synthesis of 2-deoxy-β-D-galactosides 
7. Isolation of galactosyltransferases from swine tissues. Screening of enzymatic activities
8. N-Phenyl thionocarbamates derivatives of alcohols as donors protecting groups in carbohydrate chemistry
9. Synthesis and rating of biological activity of 3,4-dichloro-2(5H)-furanone derivatives
10. Synthesis and biological activity of synthetic β-D-glucose and β-D-galactose conjugates with various acyclic nucleosides
11. Synthesis of glycosyltransferases natural substrate analogues from 1,6-anhydrosugars and acyclic uridine derivatives
12. Evaluation of cytoxicity of glycosyl uridine derivatives
13. Prediction of intestinal absorption and metabolism of biologically active genistein derivatives
14. Enzymatic synthesis of beta-2-deoxy-D-galactopyrano- sides from glycals
15. Sugars in new drug design. Sugar moiety structure as a principal determinant of antitumor glycoconjugates biological activity.
16. Glycosyl thiocarbamates in orthogonal synthesis of oligosaccharides
17. Comparison of biological activity and stability of selected C-glycosidic and O-glycosidic genistein derivatives
18. The role of a sugar moiety in new genitein derivatives affecting proliferation and apoptosis of cancer cells
19. Synthesis and in vitro screening of antiproliferative activity of C-glycosides, the derivatives of genistein and daidzein in selected cancer cell lines
20. Synthesis of galactothiophosphoesters of uridine and preliminary tests to evaluate their activity against selected glycosyltransferases
21. Application of 2-Nitroglycals in the Synthesis of Biologically Active Glycoconjugates
22. Regioselective protection of functional groups in the na- tural compounds.
23. Glycosyl O- and S- N-allyl thiocarbamates in the synthesis oligosaccharides.
24. Antiproliferative activity of novel synthetic genistein glycoside derivatives
25. (5-Nitro-2-pyridyl) 1-thioglycosides: application in synthesis of analogues of glycosyltransferases natural substrates
26. Glycoconjugates, products of uridine derivatives phosphitylation and oxidation as glycosyltransferases potential inhibitors
27. Fucosyl thiocarbamates, synthesis and application in glycosylation
28. Uridine derivatives of heteroaryl 1-thioglycosides: synthesis and biological activity against CSFV glycoproteins
29. SYNTHESIS OF URIDINE DERIVATIVES OF 2-DEOXY SUGARS AND THEIR BIOLOGICAL ACTIVITY
30. 1-THIOSUGARS: SYNTHESIS AND BIOLOGICAL ACTIVITY AGAINST CSFV GLYCOPROTEINS.