Syntheses of LewisX and Dimeric LewisX: Construction of Branched Oligosaccharides by a Combination of Preactivation and Reactivity Based Chemoselective One-Pot Glycosylations
- 16 October 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 72 (23), 8958-8961
- https://doi.org/10.1021/jo701694k
Abstract
Two asymmetrically branched oligosaccharides, LewisX and dimeric LewisX, were assembled in one pot with high yields and exclusive regio- and stereoselectivities. p-Tolyl thioglycosides were utilized as the sole type of building blocks, thus simplifying the overall synthetic design. The reactivity-independent nature of the preactivation based method allows modular assembly of the dimeric LewisX octasaccharide without the need for tedious protective group manipulation to achieve exact anomeric reactivities.Keywords
This publication has 25 references indexed in Scilit:
- Highly Efficient Syntheses of Hyaluronic Acid OligosaccharidesChemistry – A European Journal, 2006
- A Facile Method for Oxidation of Primary Alcohols to Carboxylic Acids and Its Application in Glycosaminoglycan SynthesesChemistry – A European Journal, 2006
- Iterative One‐Pot Synthesis of OligosaccharidesAngewandte Chemie, 2004
- Fluorous Thiols in Oligosaccharide Synthesis.ChemInform, 2004
- Synthesis of ganglioside epitopes for oligosaccharide specific immunoadsorption therapy of Guillian-Barré syndromeOrganic & Biomolecular Chemistry, 2004
- The Shape of Neutral ValineAngewandte Chemie, 2004
- Automated Solid‐Phase Synthesis of Protected Tumor‐Associated Antigen and Blood Group Determinant OligosaccharidesAngewandte Chemie, 2004
- Catalytic and Stereoselective Glycosylation with Glucosyl ThioformimidatesBulletin of the Chemical Society of Japan, 2003
- Reactivity-Based One-Pot Synthesis of a Lewis Y Carbohydrate Hapten: A Colon–Rectal Cancer Antigen DeterminantAngewandte Chemie, 2002
- Results and Problems of O‐Glycoside SynthesisAngewandte Chemie, 1974