7-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyloxy)-9-dihydrobaccatin III | 548484-73-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 7-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyloxy)-9-dihydrobaccatin III
• CAS: 548484-73-7
• 化学式: C₆₅H₇₄O₁₆
• 分子量: 1111.29
• InChiKey: PCHMWOLJCLGXMV-LKTLTKEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.17
• 重原子数：
  81.0
• 可旋转键数：
  19.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  204.2
• 氢给体数：
  3.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (4S,5R)-2-(4-甲氧基苯基)-4-苯基-3,5-恶唑烷二羧酸 3-叔丁酯 、 7-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyloxy)-9-dihydrobaccatin III 在 4-吡咯烷基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以93%的产率得到7-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyloxy)-9-dihydrobaccatin III-13-yl (4S,5R)-N-(t-butyloxycarbonyl)-2-(4-methoxyphenyl)-4-phenyl-5-oxazolidinecarboxylate
  参考文献：
  名称：

  Semi-Synthesis of an O -Glycosylated docetaxel analogue

  摘要：

  A 7beta-O-glycosylated docetaxel analogue was semi-synthesized from 9-dihydro-13-acetylbaccatin III, the most abundant taxane isolated from the needles of Taxus canadensis. It was shown to be more bioactive than paclitaxel according to the tubulin assay. It had a reduced potency in the MCF7 cell line cytotoxicity assay compared to paclitaxel, but it demonstrated better activity against the drug resistant cell line MCF7-ADR. In addition, the presence of one sugar moiety on C-7 doubled the water solubility versus that of paclitaxel. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00607-7
• 作为产物：
  描述：

  7-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyloxy)-9-dihydro-13-acetylbaccatin III 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 phosphate buffer 为溶剂， 反应 10.0h， 以64%的产率得到7-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyloxy)-9-dihydrobaccatin III
  参考文献：
  名称：

  Semi-Synthesis of an O -Glycosylated docetaxel analogue

  摘要：

  A 7beta-O-glycosylated docetaxel analogue was semi-synthesized from 9-dihydro-13-acetylbaccatin III, the most abundant taxane isolated from the needles of Taxus canadensis. It was shown to be more bioactive than paclitaxel according to the tubulin assay. It had a reduced potency in the MCF7 cell line cytotoxicity assay compared to paclitaxel, but it demonstrated better activity against the drug resistant cell line MCF7-ADR. In addition, the presence of one sugar moiety on C-7 doubled the water solubility versus that of paclitaxel. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00607-7