Journal of Organic Chemistry p. 4172 - 4175 (1988)
Update date:2022-09-26
Topics:
Waldman, Herbert
Kunz, Horst
The synthesis of totally protected N-acetylglucosaminylasparagine glycopeptides using the 1,3-dithian-2-ylmethyl (Dim) ester for selective C-terminal deprotection is described.Dim esters of amino acids can be conveniently synthesized by aluminum isopropoxide catalyzed transesterification of amino acid methyl esters with 1,3-dithian-2-ylmethanol or esterification of Boc amino acids with this alcohol followed by selective cleavage of the Boc group under acidic conditions.For the construction of N-glycopeptides Boc-asparatic acid α-Dim ester was synthesized and condensed with 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosylamine.The Dim group was cleaved under very mild conditions (pH 8) after oxidation of sulfur in the dithiane ring.During this reaction the Boc group, the O-acetates, and the glycoside bond remained intact.The selectively deblocked glycosylated asparagine thus obtained was condensed with amino acid Dim esters to yield totally protected glycodipeptides in high yields.
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