title: 1,2-cis Alkyl glycosides: straightforward glycosylation from unprotected 1-thioglycosyl donors.
abstract: A 1,2-cis-alkyl glycosidation protocol that makes use of unprotected phenyl 1-thioglycosyl donors is reported. Glycosylation of various functionalized alcohols was accomplished in moderate to high yield and selectivity to give the 1,2-cis-glycosides. In order to quickly develop optimum glycosylation conditions, an FIA (flow injection analysis)-ESI-TOF-MS method was developed that enabled rapid and quantitative evaluation of yield on small scale. This methodology, coupled with NMR spectroscopy, allowed for rapid evaluation of the overall reactions.
authors.affiliation: Department of Chemistry, The University of Tennessee, Knoxville, Tennessee 37996-1600, USA. dcbaker@utk.edu.
authors.forename: Bo
authors.initials: B
authors.lastname: Meng
authors.forename: Zhenqian
authors.initials: Z
authors.lastname: Zhu
authors.forename: David C
authors.initials: DC
authors.lastname: Baker
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D017022:Flow Injection Analysis / Q000379:methods; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D057166:High-Throughput Screening Assays; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism; D013865:Thioglycosides / Q000737:chemistry*
chemical_list: D000438:Alcohols; D006027:Glycosides; D013865:Thioglycosides