Protecting-group-free synthesis of 2-deoxy-aza-sugars.
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.
Dangerfield
Emma Marie
EM
Malaghan Institute of Medical Research, P.O. Box 7060, Wellington, New Zealand.
Plunkett
Catherine Heather
CH
Stocker
Bridget Louise
BL
Timmer
Mattie Simon Maria
MS
D001372:Aza Compounds / Q000138:chemical synthesis*; D002241:Carbohydrates / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
D001372:Aza Compounds; D002241:Carbohydrates