(2S,3R,4S,5R)-2-(((3S,4S,5R,6S)-5-acetoxy-4-hydroxy-6-(p-tolylthio)tetrahydro-2H-pyran-3-yl)oxy)-4,5-bis((4-methoxybenzyl)oxy)tetrahydro-2H-pyran-3-yl 4-methoxybenzoate | 1253283-84-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5R)-2-(((3S,4S,5R,6S)-5-acetoxy-4-hydroxy-6-(p-tolylthio)tetrahydro-2H-pyran-3-yl)oxy)-4,5-bis((4-methoxybenzyl)oxy)tetrahydro-2H-pyran-3-yl 4-methoxybenzoate
• CAS: 1253283-84-9
• 化学式: C₄₃H₄₈O₁₃S
• 分子量: 804.912
• InChiKey: SVKDRGJYHZXMOE-OOGGBYDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  57.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  146.67
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  三乙基氯硅烷 、 (2S,3R,4S,5R)-2-(((3S,4S,5R,6S)-5-acetoxy-4-hydroxy-6-(p-tolylthio)tetrahydro-2H-pyran-3-yl)oxy)-4,5-bis((4-methoxybenzyl)oxy)tetrahydro-2H-pyran-3-yl 4-methoxybenzoate 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 30.0h， 以70%的产率得到
  参考文献：
  名称：

  Synthesis of cholestane glycosides bearing OSW-1 disaccharide or its 1→4-linked analogue and their antitumor activities

  摘要：

  For further structure-activity relationship (SAR) research of OSW saponins, a cholestane glycoside, namely 3 beta, 16 beta, 26-trihydroxycholest-5-en-22-one 16-O-(2-O-4-methoxybenzoyl-beta-D-xylopyranosyl)-(1 -> 3)-2-O- acetyl-alpha-L-arabinopyranoside (1) together with two 1 -> 4-linked disaccharide analogues (2 and 3) were synthesized. Their cytotoxic activities were evaluated by the standard MTT assay. Compound 1 showed potent cytotoxicity against five types of human tumor cells, with IC50 ranging between 1.3 and 73 nM. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.085
• 作为产物：
  描述：

  p-methylphenyl 2-O-acetyl-1-thio-α-L-arabinopyranoside 、 Bz(4-OMe)(-2)[Mob(-3)][Mob(-4)]Xyl-O-C(NH)CCl3 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以61%的产率得到(2S,3R,4S,5R)-2-(((3S,4S,5R,6S)-5-acetoxy-4-hydroxy-6-(p-tolylthio)tetrahydro-2H-pyran-3-yl)oxy)-4,5-bis((4-methoxybenzyl)oxy)tetrahydro-2H-pyran-3-yl 4-methoxybenzoate
  参考文献：
  名称：

  Synthesis of cholestane glycosides bearing OSW-1 disaccharide or its 1→4-linked analogue and their antitumor activities

  摘要：

  For further structure-activity relationship (SAR) research of OSW saponins, a cholestane glycoside, namely 3 beta, 16 beta, 26-trihydroxycholest-5-en-22-one 16-O-(2-O-4-methoxybenzoyl-beta-D-xylopyranosyl)-(1 -> 3)-2-O- acetyl-alpha-L-arabinopyranoside (1) together with two 1 -> 4-linked disaccharide analogues (2 and 3) were synthesized. Their cytotoxic activities were evaluated by the standard MTT assay. Compound 1 showed potent cytotoxicity against five types of human tumor cells, with IC50 ranging between 1.3 and 73 nM. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.085