[(2R)-2-benzoyloxy-2-[(2S,3R)-3-benzoyloxy-2,3-dihydrofuran-2-yl]ethyl] benzoate | 191538-44-0

• 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: [(2R)-2-benzoyloxy-2-[(2S,3R)-3-benzoyloxy-2,3-dihydrofuran-2-yl]ethyl] benzoate
• CAS: 191538-44-0
• 化学式: C₂₇H₂₂O₇
• 分子量: 458.467
• InChiKey: UURXHFFLSSVUPZ-SMIHKQSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2R)-2-benzoyloxy-2-[(2S,3R)-3-benzoyloxy-2,3-dihydrofuran-2-yl]ethyl] benzoate 、 O,O-二(三甲基甲硅烷基)胸苷 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 Bz(-3)[Bz(-5)][Bz(-6)]Glcf2I(b)-thymin-1-yl
  参考文献：
  名称：

  An efficient and highly stereoselective synthesis of nucleoside derivatives from furanoid 1,2-diols

  摘要：

  Reaction between suitably protected furanoid glycals 1b-4b, readily obtained from furanoid 1,2-diols (1a-4a), and different silylated pyrimidine bases, gave the corresponding 3',5'- and 3',5',6'-O-protected 2'-deoxy-2'-iodo-beta-D-xylo-pentofuranosyl 5-10 and beta-D-gluco-hexofuranosyl 11 nucleosides, respectively. Compound 5 has been transformed into its 2'-deoxy 12 and 2',3'-anhydro 14 derivatives. The high stereoselectivity of the reaction is discussed. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00332-7
• 作为产物：
  描述：

  3,5,6-Tri-O-benzoyl-D-glucose 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到[(2R)-2-benzoyloxy-2-[(2S,3R)-3-benzoyloxy-2,3-dihydrofuran-2-yl]ethyl] benzoate
  参考文献：
  名称：

  Synthesis of furanose glycals from furanose 1,2-diols and their cyclic thiocarbonate esters

  摘要：

  Two new methods for the synthesis of furanoid glycals are described. Both procedures were shown to be faster and cheaper that those previously reported. Protected 1,2-dihydroxypento- and hexo-furanose derivatives with the D-xylo, D-gluco and D-riba, D-allo configurations were used as starting material to afford the corresponding C-3,4 D-threo and D-erythro glycals derivatives. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00072-4

文献信息

• New Method for Chloroamidation of Olefins. Application in the Synthesis of <i>N</i>-Glycopeptides and Anticancer Agents
  作者：Girish K. Rawal、Amit Kumar、Urmila Tawar、Yashwant D. Vankar

  DOI：10.1021/ol702097q

  日期：2007.12.1

  Chloroamidation of olefins using a new reagent system (COCl)(2)-AgNO3-CH3CN was observed. Various glycals with this reagent system produce 2-chloro-1-acetamido sugars in good yields which, in turn, were converted to free amino derivatives and various glycopeptides. The acetamido sugar derivatives and free amines were found to be promising anticancer agents against the U-87 malignant glyoma (a brain tumor) cell line with IC-50 = 1 nm-22 mu M, and they were found to be far less cytotoxic against a normal human embryonic kidney cell line.
• An efficient and highly stereoselective synthesis of nucleoside derivatives from furanoid 1,2-diols
  作者：Rafael Robles、concepción Rodríguez、Isidoro Izquierdo、María T. Plaza、Antonio Mota

  DOI：10.1016/s0957-4166(97)00332-7

  日期：1997.9

  Reaction between suitably protected furanoid glycals 1b-4b, readily obtained from furanoid 1,2-diols (1a-4a), and different silylated pyrimidine bases, gave the corresponding 3',5'- and 3',5',6'-O-protected 2'-deoxy-2'-iodo-beta-D-xylo-pentofuranosyl 5-10 and beta-D-gluco-hexofuranosyl 11 nucleosides, respectively. Compound 5 has been transformed into its 2'-deoxy 12 and 2',3'-anhydro 14 derivatives. The high stereoselectivity of the reaction is discussed. (C) 1997 Elsevier Science Ltd.
• Synthesis of furanose glycals from furanose 1,2-diols and their cyclic thiocarbonate esters
  作者：Rafael Robles Diaz、Concepción Rodríguez Melgarejo、Isidoro Izquierdo Cubero、María T. Plaza López-Espinosa

  DOI：10.1016/s0008-6215(97)00072-4

  日期：1997.5

  Two new methods for the synthesis of furanoid glycals are described. Both procedures were shown to be faster and cheaper that those previously reported. Protected 1,2-dihydroxypento- and hexo-furanose derivatives with the D-xylo, D-gluco and D-riba, D-allo configurations were used as starting material to afford the corresponding C-3,4 D-threo and D-erythro glycals derivatives. (C) 1997 Elsevier Science Ltd.