OpenLB
Open Library of Bioscience
Advanced Search
Tetrahedron letters
Jun 12, 2013;54 (24): 3185-3187.

An efficient and cost-effective preparation of di--acetyl-D-rhamnal.

Justin N Miller, Rongson Pongdee
Author Information
  1. Justin N Miller: Department of Chemistry, Sewanee: The University of the South, 735 University Avenue, Sewanee, TN 37383-1000, USA.
PMID: 24078748 DOI: 10.1016/j.tetlet.2013.04.035

Abstract

We have developed a synthetic route to the frequently utilized deoxysugar building block di--acetyl-D-rhamnal originating from the inexpensive starting material methyl α-D-glucopyranoside. Our approach proceeds in five steps with minimal column chromatography purification needed to afford the title compound in good overall yield. 2009 Elsevier Ltd. All rights reserved.

Keywords

carbohydrates deoxysugars glycosides natural products

References

  1. Org Biomol Chem. 2003 May 21;1(10):1690-700 [PMID: 12926356]
  2. Chem Rev. 2005 Feb;105(2):425-48 [PMID: 15700951]
  3. Angew Chem Int Ed Engl. 2007;46(14):2505-7 [PMID: 17318929]
  4. Angew Chem Int Ed Engl. 2004 May 24;43(22):2915-8 [PMID: 15170302]
  5. Org Biomol Chem. 2007 Dec 7;5(23):3847-58 [PMID: 18004466]
  6. Chem Asian J. 2010 Jun 1;5(6):1407-24 [PMID: 20480491]
  7. Chem Commun (Camb). 2006 Dec 21;(47):4952-4 [PMID: 17136258]
  8. J Org Chem. 2008 Feb 1;73(3):1036-9 [PMID: 18163646]
  9. Carbohydr Res. 2010 Jan 11;345(1):168-71 [PMID: 19892323]
  10. Chemistry. 2000 Sep 1;6(17):3095-115 [PMID: 11002992]
  11. J Am Chem Soc. 2001 Dec 19;123(50):12722-3 [PMID: 11741455]
  12. Org Lett. 2003 May 29;5(11):1875-8 [PMID: 12762675]
  13. Carbohydr Res. 1993 Feb 1;239:71-83 [PMID: 8458003]
  14. Org Lett. 2003 Oct 30;5(22):4219-22 [PMID: 14572289]
  15. Glycobiology. 1993 Apr;3(2):97-130 [PMID: 8490246]
  16. Biosci Biotechnol Biochem. 1995 Oct;59(10):1921-4 [PMID: 8534985]
  17. Org Lett. 2003 Mar 20;5(6):933-6 [PMID: 12633109]
  18. Org Lett. 2001 Nov 15;3(23):3623-6 [PMID: 11700097]
  19. Carbohydr Res. 1995 Dec 20;278(2):271-87 [PMID: 8590445]
  20. Carbohydr Res. 2010 Nov 2;345(16):2323-7 [PMID: 20883982]
  21. J Nat Prod. 2008 Feb;71(2):199-207 [PMID: 18197601]
  22. Tetrahedron. 2011 Sep 2;67(35):6524-6538 [PMID: 21804649]
  23. Angew Chem Int Ed Engl. 1999 Nov 15;38(22):3334-3339 [PMID: 10602188]
  24. Nat Prod Rep. 1997 Apr;14(2):99-110 [PMID: 9149408]
  25. Carbohydr Res. 2012 May 1;352:177-85 [PMID: 22445103]
  26. Org Lett. 2006 Jun 22;8(13):2859-61 [PMID: 16774275]
  27. Science. 1999 Apr 16;284(5413):507-11 [PMID: 10205063]
  28. Org Lett. 2008 Aug 21;10(16):3445-8 [PMID: 18630923]

Grants

  1. R15 AI084075/NIAID NIH HHS
Journal Article

Word Cloud

Created with Highcharts 10.0.0di--acetyl-D-rhamnaldevelopedsyntheticroutefrequentlyutilizeddeoxysugarbuildingblockoriginatinginexpensivestartingmaterialmethylα-D-glucopyranosideapproachproceedsfivestepsminimalcolumnchromatographypurificationneededaffordtitlecompoundgoodoverallyield2009ElsevierLtdrightsreservedefficientcost-effectivepreparationcarbohydratesdeoxysugarsglycosidesnaturalproducts

Similar Articles

Cited By