Chemoselective Synthesis of Oligosaccharides of 2-Deoxy-2-aminosugars
- 25 January 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 72 (4) , 1480-1483
- https://doi.org/10.1021/jo062171d
Abstract
Along with the application of the S-benzoxazolyl glycosides to the high-yielding synthesis of disaccharides of the 2-amino-2-deoxy series, chemoselective assembly of oligosaccharides containing multiple residues of 2-amino-2-deoxyglycoses is reported. This modified armed−disarmed approach is relying on the observation that 2-N-trichloroethoxycarbonyl derivatives of S-benzoxazolyl glycosides are significantly more reactive than their 2-N-phthaloyl counterparts in MeOTf-promoted glycosylations. This allowed efficient chemoselective synthesis of 1,2-trans-linked oligosaccharides, the disarmed reducing end of which can be activated for immediate second step glycosidation in the presence of a more powerful activator, AgOTf. As a result of this two-step activation, trans−trans-patterned trisaccharides could be assembled in a highly efficient manner. This result differs from the classic armed−disarmed technique, according to which usually cis−trans-patterned oligosaccharides are generated.Keywords
This publication has 28 references indexed in Scilit:
- Ethyl 2-acetamido-4,6-di-O-benzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-β-d-glycopyranoside as a versatile GlcNAc donorChemical Communications, 2005
- Direct and Stereoselective Synthesis of 2‐Acetamido‐2‐deoxy‐β‐D‐glycopyranosides by Using the Phosphite MethodAngewandte Chemie International Edition in English, 2005
- A Programmable One‐Pot Oligosaccharide Synthesis for Diversifying the Sugar Domains of Natural Products: A Case Study of VancomycinAngewandte Chemie International Edition in English, 2003
- Oxazolidinone Protected 2-Amino-2-deoxy-d-glucose Derivatives as Versatile Intermediates in Stereoselective Oligosaccharide Synthesis and the Formation of α-Linked GlycosidesJournal of the American Chemical Society, 2001
- Syntheses of Anomerically Phosphodiester-Linked Oligomers of the Repeating Units of the Haemophilus influenzae Types c and f Capsular PolysaccharidesThe Journal of Organic Chemistry, 2001
- Synthesis of Asialo GM1. New Insights in the Application of Sulfonamidoglycosylation in Oligosaccharide Assembly: Subtle Proximity Effects in the Stereochemical Governance of GlycosidationJournal of the American Chemical Society, 1998
- Glycosphingolipid antigens and cancer therapyChemistry & Biology, 1997
- Two New Orthogonal Amine-Protecting Groups that can be Cleaved under Mild or Neutral ConditionsJournal of the American Chemical Society, 1995
- Synthesis of oligosaccharides of 2-amino-2-deoxy sugarsChemical Reviews, 1992
- The Synthesis of Silacyclopentane DerivativesBulletin of the Chemical Society of Japan, 1972