title: Protecting-group-free synthesis of 2-deoxy-aza-sugars.
abstract: The protecting-group-free asymmetric synthesis of 1,2,4-trideoxy-1,4-imino-L-xylitol is readily achieved in five steps from 2-deoxy-D-ribose and with an overall yield of 48%. Key in this synthesis is the application of our recently developed Vasella-reductive amination and carbamate annulation methodologies to the synthesis of 2-deoxy-aza-sugars. The carbamate annulation occurred with excellent yield and diastereoselectively (>20:1 d.r.), in favour of the 3,4-cis isomer.
authors.affiliation: Malaghan Institute of Medical Research, P.O. Box 7060, Wellington, New Zealand.
authors.forename: Emma Marie
authors.initials: EM
authors.lastname: Dangerfield
authors.forename: Catherine Heather
authors.initials: CH
authors.lastname: Plunkett
authors.forename: Bridget Louise
authors.initials: BL
authors.lastname: Stocker
authors.forename: Mattie Simon Maria
authors.initials: MS
authors.lastname: Timmer
mesh_terms: D001372:Aza Compounds / Q000138:chemical synthesis*; D002241:Carbohydrates / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
chemical_list: D001372:Aza Compounds; D002241:Carbohydrates