Stereoselective synthesis of UDP-2-(2-ketopropyl)galactose aided by di-tert-butylsilylene protecting group
Yasuharu Sakamoto1, Tsuyoshi Ohta2, Yukishige Ito3,4
1Synthetic Cellular Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. ysakamot@riken.jp.
Abstract:
UDP-2-(2-ketopropyl)galactose (1) has been utilized as a valuable probe for profiling proteins modified by O-GlcNAc. In this work, we developed a protocol for efficient synthesis of 1. Thus, 2-methallylgalactose derivative 11, a synthetic intermediate for the compound 1, was prepared by stereoselective iodination and methallylation at C-2 position, through exploitation of 4,6-O-di-tert-butylsilylene protecting group.
Related Concept Videos
Biosynthesis of Polysaccharides
SN2 Reaction: Stereochemistry
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
Oligosaccharide Assembly
Multiple sugar molecules that may or may...
Sharpless Epoxidation
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Alkylation of β-Diester Enolates: Malonic Ester Synthesis


