(7S)-3,6-anhydro-1,2:4,5-di-O-isopropylidene-7-C-phenyl-D-glycero-D-manno-heptitol | 201863-39-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (7S)-3,6-anhydro-1,2:4,5-di-O-isopropylidene-7-C-phenyl-D-glycero-D-manno-heptitol
• 英文别名: (S)-[(3aR,4R,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-phenylmethanol
• CAS: 201863-39-0
• 化学式: C₁₉H₂₆O₆
• 分子量: 350.412
• InChiKey: KTGNOTOJCPZHHM-IZKTWJBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (7S)-3,6-anhydro-1,2:4,5-di-O-isopropylidene-7-C-phenyl-D-glycero-D-manno-heptitol 在 sodium hydride 、 溶剂黄146 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 20.5h， 生成 (7S)-3,6-anhydro-7-O-benzyl-1,2-dideoxy-4,5-O-isopropylidene-7-C-phenyl-D-altro-hept-1-enitol
  参考文献：
  名称：

  Synthesis and antitumor activity of goniofufurone analogues

  摘要：

  Synthesis and antitumor activity of goniofufurone analogues 15, 16, 17, 33, and 46 is reported. Key step in the synthesis is Pd (II) mediated oxidative cyclisation of vinyl-(hydroxy) furans 18, 19 to the corresponding lactols 32, 43. Cytotoxicities of 15, 16, 17, 33, and 46 tested against six human cancer cell lines are reported. Change of stereochemistry at C-5, C-6 and C-7 position of goniofufurone (1) did not enhance the cytotoxicities significantly.

  DOI：

  10.1016/s0968-0896(99)00164-9
• 作为产物：
  描述：

  (7S)-3,6-anhydro-1,2:4,5-di-O-isopropylidene-7-C-phenyl-7-O-(4-nitrobenzoyl)-D-glycero-D-manno-heptitol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以93%的产率得到(7S)-3,6-anhydro-1,2:4,5-di-O-isopropylidene-7-C-phenyl-D-glycero-D-manno-heptitol
  参考文献：
  名称：

  Synthesis and antitumor activity of goniofufurone analogues

  摘要：

  Synthesis and antitumor activity of goniofufurone analogues 15, 16, 17, 33, and 46 is reported. Key step in the synthesis is Pd (II) mediated oxidative cyclisation of vinyl-(hydroxy) furans 18, 19 to the corresponding lactols 32, 43. Cytotoxicities of 15, 16, 17, 33, and 46 tested against six human cancer cell lines are reported. Change of stereochemistry at C-5, C-6 and C-7 position of goniofufurone (1) did not enhance the cytotoxicities significantly.

  DOI：

  10.1016/s0968-0896(99)00164-9

文献信息

• Synthesis and antitumor activity of goniofufurone analogues
  作者：Hari Babu Mereyala、Rajendrakumar Reddy Gadikota、Maju Joe、Sudershan K. Arora、Sunanda G. Dastidar、Sudhanshu Agarwal

  DOI：10.1016/s0968-0896(99)00164-9

  日期：1999.9

  Synthesis and antitumor activity of goniofufurone analogues 15, 16, 17, 33, and 46 is reported. Key step in the synthesis is Pd (II) mediated oxidative cyclisation of vinyl-(hydroxy) furans 18, 19 to the corresponding lactols 32, 43. Cytotoxicities of 15, 16, 17, 33, and 46 tested against six human cancer cell lines are reported. Change of stereochemistry at C-5, C-6 and C-7 position of goniofufurone (1) did not enhance the cytotoxicities significantly.