123672-99-1Relevant academic research and scientific papers
Synthesis of novel optically active cyclic phospholipid conjugates of Tegafur and uridine starting from L-serine
He, Zheng-Jie,Chen, Wen-Bin,Zhang, Cheng-Xiang,Zhou, Zheng-Hong,Tang, Chu-Chi
, p. 223 - 232 (2000)
Starting from L-serine, cyclic thiophosphoramidate conjugates (2 and 3) of Tegatur and uridine were synthesized via a multiple-step procedure of esterification, cyclic phosphorylation, and sulfurization, etc. L-serinoate was N-alkylated, then cyclized with phosphorus oxychloride, and further reacted with N3-(2-hydroxyethyl) Tegafur to afford cyclic phospholipid conjugate 4. The resultants (2, 3, and 4) were successfully separated in the form of pure diastereomer by column chromatography on silica gel. Their configurations were discussed and assigned according to their NMR spectra. The asymmetric induction effects of the carbon-based chiral centre on the diastereomer preference were also observed in these two synthetic phosphorylation cyclizations. The bioassay on their antitumor activities is under investigation.
Synthesis of novel optically active cyclic phospholipid conjugates of tegafur and uridine starting from L-serine
He, Zheng-Jie,Chen, Wen-Bin,Zhang, Cheng-Xiang,Zhou, Zheng-Hong,Tang, Chu-Chi
, p. 903 - 909 (2007/10/03)
Starting from L-serine, cyclic phospholids 2,3 and 4 were synthesized and successfully separated in the form of pure diastereomer. Their configurations were discussed and assigned according to their NMR spectra data. The asymmetric induction effects were
Synthesis, Configuration, and Chemical Shift Correlations of Chiral 1,3,2-Oxazaphospholidin-2-ones Derived from l-Serine
Thompson,Charles M.,Frick, Jeffrey A.,Green, Diana L.C.
, p. 111 - 116 (2007/10/02)
The reaction between (S)-methyl N-benzylserinoate and phosphorous oxychloride leads to the diastereomeric chloro-1,3,2-oxazaphospholidin-2-ones.Reaction of the chloridates with alcohols or phenols in the presence of base affords the corresponding alkoxy (or aryloxy) derivatives (66-94percent), which were readily separated by standard chromatographic methods.The stereochemical arrangement of these compounds was established by NMR chemical shift correlations (carbon-13 and phosphorus-31) and single-crystal X-ray analysis.The trans geometry of the carbomethoxy and exocyclicphosphorus ligand resulted in approximately a 1 ppm upfield shift in the phosphorus-31 spectra relative to the cis isomer.The carbon-13 NMR spectra revealed an opposite trend to the heteroatom-bound alkyl region with most of the trans isomer signals appearing downfield (0.2-1.2 ppm) from the corresponding cis isomer.
