Synthesis and characterization of stereoisomers of 5,6-dihydro-5,6-dihydroxy-thymidine.
Six products were isolated by reverse phase HPLC from the reaction of thymidine with osmium tetroxide. Four of the products were identified as stereoisomers of 5,6-dihydro-5,6-dihydroxy-thymidine (TG). The absolute configurations of these four compounds (from the shortest to the longest HPLC retention times) were determined by two-dimensional nuclear magnetic resonance spectroscopy to be (-)-trans-5S,6S-, (+)-trans-5R,6R-, (-)-cis-5R,6S-, and (+)-cis-5S,6R-5,6-dihydro-5,6-dihydroxy-thymidine. The other two products were dimers with unknown linking sites. Parameters of the mass and nuclear magnetic resonance spectra are reported and discussed.
Vaishnav
Y
Y
Radiation Biochemistry Department, Armed Forces Radiobiology Research Institute, Bethesda, MD 20889-5154.
Holwitt
E
E
Swenberg
C
C
Lee
H C
HC
Kan
L S
LS
D002851:Chromatography, High Pressure Liquid; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009993:Osmium Tetroxide / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature; D013936:Thymidine / Q000031:analogs & derivatives* / Q000737:chemistry
C029390:thymidine glycol; D009993:Osmium Tetroxide; D013936:Thymidine