methyl (4S)-3-benzyl-2-chloro-2-oxo-1,3,2λ5-oxazaphospholidine-4-carboxylate | 123621-73-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (4S)-3-benzyl-2-chloro-2-oxo-1,3,2λ5-oxazaphospholidine-4-carboxylate
• CAS: 123621-73-8；123672-99-1
• 化学式: C₁₁H₁₃ClNO₄P
• 分子量: 289.655
• InChiKey: ZURSFYNNLCQSIW-APDXDRDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (4S)-3-benzyl-2-chloro-2-oxo-1,3,2λ5-oxazaphospholidine-4-carboxylate 在 sodium methylate 、 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 Methyl (2R,4S)-2-Methoxy-2-oxo-(anti)-3-benzyl-1,3,2-oxazaphospholidine-4-carboxylate
  参考文献：
  名称：

  Synthesis, configuration, and chemical shift correlations of chiral 1,3,2-oxazaphospholidin-2-ones derived from l-serine

  摘要：

  DOI：

  10.1021/jo00288a023
• 作为产物：
  描述：

  L-N-苄基丝氨酸甲酯 在 三乙胺 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以94.7%的产率得到methyl (4S)-3-benzyl-2-chloro-2-oxo-1,3,2λ5-oxazaphospholidine-4-carboxylate
  参考文献：
  名称：

  Synthesis of Novel Optically Active Cyclic Phospholipid Conjugates of Tegafur and Uridine Starting From L-Serine

  摘要：

  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 also observed in two phosphorylation cyclizations.

  DOI：

  10.1080/00397910008087103

文献信息

• SYNTHESIS OF NOVEL OPTICALLY ACTIVE CYCLIC PHOSPHOLIPID CONJUGATES OF TEGAFUR AND URIDINE STARTING FROM L-SERINE
  作者：Zheng-Jie He、Wen-Bin Chen、Cheng-Xiang Zhang、Zheng-Hong Zhou And、Chu-Chi Tang

  DOI：10.1080/10426500008043682

  日期：2000.5.1

  Starting from L-serine, cyclic thiophosphoramidate conjugates (2 and 3) of Tegafur 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 N-3-(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.
• THOMPSON, CHARLES M.;FRICK, JEFFREY A.;GREEN, DIANA L. C., J. ORG. CHEM., 55,(1990) N, C. 111-116
  作者：THOMPSON, CHARLES M.、FRICK, JEFFREY A.、GREEN, DIANA L. C.

  DOI：——

  日期：——