0000000000394000
AUTHOR
Stefan Henke
Combinatorial solid-phase synthesis using D-galactose as a chiral five-dimension-deversity scaffold
Abstract All five hydroxy groups of galactose as the scaffold are used for selective coupling of side chains in a combinatorial methodology by application of a set of orthogonally stable protecting groups in combination with a thioglycoside anchor.
d-Glucose as a multivalent chiral scaffold for combinatorial chemistry
Due to their high density of functional groups and their availability in a variety of diastereomeric forms, monosaccharides are considered attractive scaffolds for combinatorial chemistry that allow the attachment and defined spatial alignment of up to five different pharmacophoric groups. For their application in combinatorial syntheses on solid phase, a set of selectively removable hydroxy protecting groups in combination with a cleavable anchor is required. Herein, we report on the construction and use of a versatile multivalent glucose building block for parallel synthesis on the solid phase.
D-Glucose as a Pentavalent Chiral Scaffold
A novel carbohydrate-based scaffold for combinatorial chemistry has been developed. This scaffold allows the selective attachment of five different side chains, giving rise to products of enormous structural diversity. As a demonstration of its usefulness, a series of model compounds has been prepared in high purity and yield by multistep parallel synthesis on a solid phase. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
CCDC 813647: Experimental Crystal Structure Determination
Related Article: Till Opatz, Christopher Kallus, Tobias Wunberg, Wolfgang Schmidt, Stefan Henke, Horst Kunz|2002|Carbohydr.Res.|337|2089|doi:10.1016/S0008-6215(02)00301-4