gem-Dimethyl 4-pentenyl glycosides: novel glycosylating agents and anomeric protecting groups.
Two classes of gem-dimethyl 4-n-pentenyl glycosides (i.e., C2-series and C3-series) have been prepared and studied in both the glycosylation and hydrolysis manifolds utilizing NBS as the sole stoichiometric activator. These novel glycosylating agents, which are analogues of Fraser-Reid's 4-n-pentenyl glycosyl donors, show increased reactivity in side-by-side studies by virtue of the gem-dimethyl effect.
Fortin
Michael
M
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA.
Kaplan
Justin
J
Pham
Khoa
K
Kirk
Sharon
S
Andrade
Rodrigo B
RB
D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006868:Hydrolysis; D015394:Molecular Structure; D013237:Stereoisomerism
D006027:Glycosides