title: Convenient stereocontrolled amidoglycosylation of alcohols with acetylated glycals and trichloroethoxysulfonamide.
abstract: A regio- and stereo-controlled, rhodium(II)-catalyzed amidoglycosylation of alcohols has been developed using O-acetylated glycals, trichloroethoxysulfonamide, and iodosobenzene. This one-pot amidoglycosylation was applied to a variety of primary and secondary alcohols to afford the β-O-glycosides with acceptable yields up to 84%. The reaction would proceed via stereoselective intermolecular aziridination of the glycal from the α-face followed by SN2 reaction with alcohol at C-1 from the β-face to give 1,2:2,3-di-trans-substituted isomer only.
authors.affiliation: Health Research Institute, National Institute of Advanced Industrial Science and Technology (AIST) Tsukuba Central 6, Tsukuba, Ibaraki 305-8566, Japan. Electronic address: t-murakami@aist.go.jp.
authors.forename: Teiichi
authors.initials: T
authors.lastname: Murakami
authors.affiliation: Research Institute for Energy Conservation, National Institute of Advanced Industrial Science and Technology (AIST) Tsukuba Central 2, Tsukuba, Ibaraki 305-8562, Japan.
authors.forename: Yukari
authors.initials: Y
authors.lastname: Sato
authors.affiliation: Biomedical Research Institute, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 6, Tsukuba, Ibaraki 305-8566, Japan.
authors.forename: Kyoko
authors.initials: K
authors.lastname: Yoshioka
authors.affiliation: Health Research Institute, National Institute of Advanced Industrial Science and Technology (AIST) Tsukuba Central 6, Tsukuba, Ibaraki 305-8566, Japan.
authors.forename: Mutsuo
authors.initials: M
authors.lastname: Tanaka
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000577:Amides / Q000737:chemistry*; D006031:Glycosylation; D007462:Iodobenzenes / Q000737:chemistry; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000577:Amides; D007462:Iodobenzenes; D013449:Sulfonamides; D012238:Rhodium; C037276:iodosobenzene
keywords: 12-Bromo-1-dodecanol (PubChem CID: 137895); 2,2,2-Trichloroethoxysulfonamide (PubChem CID: 3052707); Amidoglycosylation; Aziridination; ChloroBenzene (PubChem CID: 79645); Glycals; Hexa-O-Acetyl-lactal (PubChem CID: 2734746); Iodosobenzene (PubChem CID: 92125); Nitrene; Stereocontrol; Tri-O-Acetyl-D-galactal (PubChem CID: 640125); Tri-O-Acetyl-D-glucal (PubChem CID: 688303)