2-tosyloxy-3-[(tert-butyldiphenylsilyl)oxy]-4-methoxybenzaldehyde | 1242074-07-2

• 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: 2-tosyloxy-3-[(tert-butyldiphenylsilyl)oxy]-4-methoxybenzaldehyde
• 英文别名: [2-[Tert-butyl(diphenyl)silyl]oxy-6-formyl-3-methoxyphenyl] 4-methylbenzenesulfonate
• CAS: 1242074-07-2
• 化学式: C₃₁H₃₂O₆SSi
• 分子量: 560.743
• InChiKey: AXCSVYSTJDKRGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-tosyloxy-3-[(tert-butyldiphenylsilyl)oxy]-4-methoxybenzaldehyde 、 三苯基-(3,4,5-三甲氧基-苄基)-溴化膦 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以64%的产率得到[2-[tert-butyl(diphenyl)silyl]oxy-3-methoxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl] 4-methylbenzenesulfonate
  参考文献：
  名称：

  Regio- and Stereospecific Synthesis of Mono-β-d-Glucuronic Acid Derivatives of Combretastatin A-1

  摘要：

  Synthetic routes have been established for the preparation of regio- and stereoisomerically pure samples of the mono-beta-D-glucuronic acid derivatives of combretastatin A-1, referred to as CA1G1 (5a) and CA1G2 (6a). Judicious choice of protecting groups for the catechol ring was required for the regiospecific introduction of the glucuronic acid moiety. The tosyl group proved advantageous in this regard. The two monoglucuronic acid analogues demonstrate low cytotoxicity (compared to CA1, 2) against selected human cancer cell lines, with CA1G1 being slightly more potent than CA1G2.

  DOI：

  10.1021/np100108e
• 作为产物：
  描述：

  2-hydroxy-3-[(tert-butyldiphenylsilyl)oxy]-4-methoxybenzaldehyde 、 对甲苯磺酰氯 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以93%的产率得到2-tosyloxy-3-[(tert-butyldiphenylsilyl)oxy]-4-methoxybenzaldehyde
  参考文献：
  名称：

  Regio- and Stereospecific Synthesis of Mono-β-d-Glucuronic Acid Derivatives of Combretastatin A-1

  摘要：

  Synthetic routes have been established for the preparation of regio- and stereoisomerically pure samples of the mono-beta-D-glucuronic acid derivatives of combretastatin A-1, referred to as CA1G1 (5a) and CA1G2 (6a). Judicious choice of protecting groups for the catechol ring was required for the regiospecific introduction of the glucuronic acid moiety. The tosyl group proved advantageous in this regard. The two monoglucuronic acid analogues demonstrate low cytotoxicity (compared to CA1, 2) against selected human cancer cell lines, with CA1G1 being slightly more potent than CA1G2.

  DOI：

  10.1021/np100108e

文献信息

• Regio- and Stereospecific Synthesis of Mono-β-<scp>d</scp>-Glucuronic Acid Derivatives of Combretastatin A-1
  作者：Rajendra P. Tanpure、Tracy E. Strecker、David J. Chaplin、Bronwyn G. Siim、Mary Lynn Trawick、Kevin G. Pinney

  DOI：10.1021/np100108e

  日期：2010.6.25

  Synthetic routes have been established for the preparation of regio- and stereoisomerically pure samples of the mono-beta-D-glucuronic acid derivatives of combretastatin A-1, referred to as CA1G1 (5a) and CA1G2 (6a). Judicious choice of protecting groups for the catechol ring was required for the regiospecific introduction of the glucuronic acid moiety. The tosyl group proved advantageous in this regard. The two monoglucuronic acid analogues demonstrate low cytotoxicity (compared to CA1, 2) against selected human cancer cell lines, with CA1G1 being slightly more potent than CA1G2.