Practical synthesis of (2'R)-2'-deoxy-2'-C-methyluridine by highly diastereoselective homogeneous hydrogenation.
Diastereoselective hydrogenation of 2'-deoxy-2'-exo-methyleneuridine was carried out under homogeneous conditions using a low loading of a chiral Rh catalyst. This, coupled with improvements in the synthesis of the substrate, allowed the smooth pilot plant preparation of the title compound on >10 kg scale.
Johnson and Johnson Pharmaceutical Development, Turnhoutseweg 30, B-2340 Beerse, Belgium. slemaire@its.jnj.com
Sébastien
S
Lemaire
Ioannis
I
Houpis
Rainer
R
Wechselberger
Jaak
J
Langens
Wim A A
WA
Vermeulen
Nico
N
Smets
Ulrike
U
Nettekoven
Youchu
Y
Wang
Tingting
T
Xiao
Haisheng
H
Qu
Renmao
R
Liu
Tim H M
TH
Jonckers
Pierre
P
Raboisson
Koen
K
Vandyck
Karl M
KM
Nilsson
Vittorio
V
Farina
D002384:Catalysis; D006865:Hydrogenation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
C553247:(2'S)-2'-deoxy-2'-C-methyluridine; C516788:2'-C-methyluridine; D014529:Uridine