5-O-(4-chlorobenzoyl)-1,2-O-isopropylidene-D-erythro-pentofuranose03-urose | 199787-15-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-O-(4-chlorobenzoyl)-1,2-O-isopropylidene-D-erythro-pentofuranose03-urose
• 英文别名: 5-O-(4-chlorobenzoyl)-1,2-O-isopropylidene-α-D-pentofuranose-3-urose；[(3aR,5R,6aS)-2,2-dimethyl-6-oxo-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-5-yl]methyl 4-chlorobenzoate
• CAS: 199787-15-0
• 化学式: C₁₅H₁₅ClO₆
• 分子量: 326.733
• InChiKey: AAXHZFRYIVQGPS-MPKXVKKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-O-(4-chlorobenzoyl)-1,2-O-isopropylidene-D-erythro-pentofuranose03-urose 在 甲酸 、 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 3.25h， 生成 5-O-(4-chlorobenzoyl)-3-C-[2-(trimethylsilyl)ethynyl]-D-ribo-pentofuranose
  参考文献：
  名称：

  Nucleosides and nucleotides. Part 212: Practical large-scale synthesis of 1-(3-C-ethynyl-β-d-ribo-pentofuranosyl)cytosine (ECyd), a potent antitumor nucleoside. Isobutyryloxy group as an efficient anomeric leaving group in the Vorbrüggen glycosylation reaction

  摘要：

  A practical synthetic route to the antitumor nucleoside, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd, 1) from 1,2-O-isopropylidene-D-xylofuranose (3) has been developed. Since most of the compounds were obtained as crystals, the target ECyd was prepared without any chromatographic purification in 31% overall yield from compound 3. The isobutyryloxy group was found to be an effective leaving group at the anomeric position of the 3-beta-C-ethynyl glycosyl donors in the key Vorbruggen glycosylation reaction. Using a similar procedure without chromatographic purification, the uracil congener EUrd [1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)uracil (2), which also has a potent antitumor effect, was synthesized from 3 in 39% overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01249-2
• 作为产物：
  描述：

  5-O-(4-chlorobenzoyl)-1,2-O-isopropylidene-D-xylofuranose 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 tri-chlorocyanuric acid 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以77%的产率得到5-O-(4-chlorobenzoyl)-1,2-O-isopropylidene-D-erythro-pentofuranose03-urose
  参考文献：
  名称：

  受保护的核苷3'-磷酸的膦硫代二氟亚甲基类似物的第二代合成

  摘要：

  描述了一种实用的八步合成关键中间体14的方法，该方法可从α-d-木糖获得19％的总收率。制备可以以克为单位进行，并且涉及有机镁试剂2d的使用。制备15可证明衍生物14转化为标题化合物的能力。此外，中间体12的X射线晶体学提供了有关二氟硫代磷酸酯的第一结构数据。

  DOI：

  10.1016/j.tet.2004.03.082

文献信息

• 10.1021/acs.joc.4c00671
  作者：Yuan, Shaopan、Pei, Wanqing、Di, Xuan、Qin, Yali、Jin, Hongming、Meng, Zhanchao、Hou, Xiaoli

  DOI：10.1021/acs.joc.4c00671

  日期：——

  The total synthesis of (−)-piericone D, a potential antithrombotic dihydrochalcone featuring an [3.3.0] octane core, is reported. Salient features of our synthesis include a stereoselective β-O-glycosylation to install the asebogenin aglycone and a late-stage global deprotection followed by simultaneous lactonization. The convergent synthesis paved the way for further structure–activity relationship

  报道了 （-）-piericone D 的全合成，这是一种具有 [3.3.0] 辛烷核心的潜在抗血栓二氢查尔酮。我们合成的显着特点包括立体选择性 β-O-糖基化以安装 asebogenin 糖苷配基，以及后期整体脱保护，然后同时进行内酯化。收敛合成为 （-）-piericone D 的进一步构效关系 （SAR） 研究铺平了道路。
• Second-generation synthesis of protected phosphonothiodifluoromethylene analogues of nucleoside-3′-phosphates
  作者：Irina Kalinina、Arnaud Gautier、Carmen Salcedo、Jean-Yves Valnot、Serge R Piettre

  DOI：10.1016/j.tet.2004.03.082

  日期：2004.5

  A practical, eight-step synthesis of the key intermediate 14 in 19% overall yield from α-d-xylose is described. The preparation can be carried out on multi-gram scale and involves the use of the organomagnesium reagent 2d. The capability of derivative 14 to be transformed into the title compounds is examplified by the preparation of 15. Additionally, X-ray crystallography of intermediate 12 provided

  描述了一种实用的八步合成关键中间体14的方法，该方法可从α-d-木糖获得19％的总收率。制备可以以克为单位进行，并且涉及有机镁试剂2d的使用。制备15可证明衍生物14转化为标题化合物的能力。此外，中间体12的X射线晶体学提供了有关二氟硫代磷酸酯的第一结构数据。
• Nucleosides and nucleotides. Part 212: Practical large-scale synthesis of 1-(3-C-ethynyl-β-d-ribo-pentofuranosyl)cytosine (ECyd), a potent antitumor nucleoside. Isobutyryloxy group as an efficient anomeric leaving group in the Vorbrüggen glycosylation reaction
  作者：Makoto Nomura、Tsutomu Sato、Masato Washinosu、Motoaki Tanaka、Tetsuji Asao、Satoshi Shuto、Akira Matsuda

  DOI：10.1016/s0040-4020(01)01249-2

  日期：2002.2

  A practical synthetic route to the antitumor nucleoside, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd, 1) from 1,2-O-isopropylidene-D-xylofuranose (3) has been developed. Since most of the compounds were obtained as crystals, the target ECyd was prepared without any chromatographic purification in 31% overall yield from compound 3. The isobutyryloxy group was found to be an effective leaving group at the anomeric position of the 3-beta-C-ethynyl glycosyl donors in the key Vorbruggen glycosylation reaction. Using a similar procedure without chromatographic purification, the uracil congener EUrd [1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)uracil (2), which also has a potent antitumor effect, was synthesized from 3 in 39% overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.