2-O-acetyl-3,4-bis-O-(triethylsilyl)-l-arabino-pyranosyl trichloroacetimidate | 721959-15-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-acetyl-3,4-bis-O-(triethylsilyl)-l-arabino-pyranosyl trichloroacetimidate
• 英文别名: [(3R,4R,5S)-2-(2,2,2-trichloroethanimidoyl)oxy-4,5-bis(triethylsilyloxy)oxan-3-yl] acetate
• CAS: 721959-15-5
• 化学式: C₂₁H₄₀Cl₃NO₆Si₂
• 分子量: 565.082
• InChiKey: BWFNKDMWHNSVPV-HTUJPFKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  87.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-O-acetyl-3,4-bis-O-(triethylsilyl)-l-arabino-pyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 氟化氢吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 dodecyl (2S)-2-[(3S,8R,9S,10R,13S,14S,16S,17S)-16-[(2S,3R,4S,5S)-3-acetyloxy-4,5-dihydroxyoxan-2-yl]oxy-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl]propanoate
  参考文献：
  名称：

  Synthesis of OSW saponin analogs with modified sugar residues and their antiproliferative activities

  摘要：

  Eight monosaccharide analogs of the potent antitumor OSW saponins (2-9) were synthesized. One analog, 2-O-acetyl-aL-arabinopyranoside 3, showed antiproliferative activity against the Jurkat cells (IC50 = 0.078 mu M) comparable to that of the disaccharide derivative (1). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.032
• 作为产物：
  描述：

  acetic acid 4,5-dihydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester 在 2,6-二甲基吡啶 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 生成 2-O-acetyl-3,4-bis-O-(triethylsilyl)-l-arabino-pyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of OSW saponin analogs with modified sugar residues and their antiproliferative activities

  摘要：

  Eight monosaccharide analogs of the potent antitumor OSW saponins (2-9) were synthesized. One analog, 2-O-acetyl-aL-arabinopyranoside 3, showed antiproliferative activity against the Jurkat cells (IC50 = 0.078 mu M) comparable to that of the disaccharide derivative (1). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.032

文献信息

• Synthesis of analogues of a potent antitumor saponin OSW-1
  作者：Jacek W. Morzycki、Agnieszka Wojtkielewicz、Sławomir Wołczyński

  DOI：10.1016/j.bmcl.2004.03.102

  日期：2004.6

  A series of side chain analogues (5a-e), a 22-glycosylated isomer (10), and 16beta-O-l-arabinosyl (13a) or 16beta-O-d-xylosyl (13b) analogues of OSW-1 were synthesized. All analogues were found to be less cytotoxic against breast and endometrial cancer cell lines than the natural product.

  合成了一系列OSW-1的侧链类似物（5a-e），22-糖基化的异构体（10）和16beta-O1-阿拉伯糖基（13a）或16beta-Od-木糖基（13b）类似物。发现所有类似物对乳腺癌和子宫内膜癌细胞系的细胞毒性均小于天然产物。