ChemInform Abstract: Synthesis of a New Class of N-Linked Lewis and LacNAc Analogues as Potential Inhibitors of Human Fucosyltransferases: A General Method for the Incorporation of an Iminocyclitol as a Transition-State Mimetic of the Donor Sugar to the Acceptor.
✍ Scribed by Ralf Wischnat; Richard Martin; Chi-Huey Wong
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 35 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Synthesis of a New Class of N-Linked Lewis and LacNAc Analogues as Potential Inhibitors of Human Fucosyltransferases: A General Method for the Incorporation of an Iminocyclitol as a Transition-State Mimetic of the Donor Sugar to the Acceptor.
-The synthesis of the title N-linked di-and trisaccharides involves transformation of glucosamine derivative (I) to the azido sugar (VI) under excellent stereocontrol, the coupling of sugar (VI) with imidate (VII) to produce the desired disaccharide (VIII) as a single isomer, and reductive amination of aldehyde (X) (derived from the iminocyclitol) with amine (IX) to give the target trisaccharide (XI). Since the amination of (X) with the amine provided from reduction of azide (VI) also gives the corresponding disaccharide this procedure represents a general strategy for the incorporation of an iminocyclitol. -(WISCHNAT, RALF;