title: Stereoselective synthesis of UDP-2-(2-ketopropyl)galactose aided by di-tert-butylsilylene protecting group.
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.
authors: Synthetic Cellular Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. ysakamot@riken.jp.
authors: Yasuharu
authors: Y
authors: Sakamoto
authors: Synthetic Cellular Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
authors: Tsuyoshi
authors: T
authors: Ohta
authors: Synthetic Cellular Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. yukito@riken.jp.|Japan Science and Technology Agency (JST), ERATO Glycotrilogy Project, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. yukito@riken.jp.
authors: Yukishige
authors: Y
authors: Ito
mesh_terms: D000118:Acetylglucosaminidase / Q000737:chemistry / Q000378:metabolism*; D002073:Butanes / Q000737:chemistry*; D005690:Galactose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D017351:N-Acetylglucosaminyltransferases / Q000737:chemistry; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002073:Butanes; D012821:Silanes; C512229:di-tert-butylsilylene; D017351:N-Acetylglucosaminyltransferases; C449880:O-GlcNAc transferase; D000118:Acetylglucosaminidase; D005690:Galactose
keywords: Di-tert-butylsilylene; Galactose derivative; Iodination; Radical methallylation; Stereoselective synthesis