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2005
Carbohydrates
U 0500
Hexafluoroacetone as Protecting and Activating Reagent. Glycosylated Malic,
and Thiomalic Acid Derivatives, New Glycosylated Building Blocks
06- 180 Citramalic,
for Drug Design. — The new building blocks (VI) are synthesized for glycopeptide
modification, testing new protection/activation concepts like the "hexafluoroacetone
route". Glycosylated α-hydroxy acid derivatives (VI) undergo an intramolecular cyclocondensation upon treatment with bases to give stereoselectively succinimido sugars
(VII). Stronger bases such as DBU cause the formation of an additional sugar, maleimido sugar (IX). Moreover, hexafluoroacetone-protected α-hydroxy acids (VI) are
excellent acyl transfer reagents. These compounds react with amino acid and dipeptide
esters or amides like (X) to give N-glycoconjugates (XI), which are of potential use as
building blocks for the construction of glycosylated depsipeptides. —
(BOETTCHER, C.; SPENGLER, J.; BURGER*, K.; Monatsh. Chem. 135 (2004) 10,
1225-1242; Inst. Org. Chem., Univ. Leipzig, D-04103 Leipzig, Germany; Eng.) —
H. Hoennerscheid
2005
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