ditert-butyl (2S,3R)-2-hydroxy-2-[2-[(4-methoxyphenyl)methoxy]ethyl]-3-prop-2-enylbutanedioate | 1073862-07-3

• 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: ditert-butyl (2S,3R)-2-hydroxy-2-[2-[(4-methoxyphenyl)methoxy]ethyl]-3-prop-2-enylbutanedioate
• CAS: 1073862-07-3
• 化学式: C₂₅H₃₈O₇
• 分子量: 450.573
• InChiKey: RDYKWAGWDVLXJI-CPJSRVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-叔丁基-1,3-二异丙基异脲 、 以 二氯甲烷 为溶剂， 生成 (2S,3S)-di-tert-butyl 2-(2-(4-methoxybenzyloxy)ethyl)-3-allyl-2-hydroxysuccinate 、 ditert-butyl (2S,3R)-2-hydroxy-2-[2-[(4-methoxyphenyl)methoxy]ethyl]-3-prop-2-enylbutanedioate
  参考文献：
  名称：

  Asymmetric synthesis of (+)-trachyspic acid

  摘要：

  Aldol reaction of di-tert-butyl 4-(4-methoxybenzyloxy)-2-oxobutanoate with pent-4-enal using (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea hydrochloride as a catalyst, followed by Pinnick oxidation and tert-butyl esterification, gave (2S,3S)-di-tert-butyl 2-(2-(4-methoxybenzyloxy)ethyl)-3-allyl-2-hydroxysuccinate in high optical purity (85% ee), from which the total synthesis of (+)-trachyspic acid, a tumor cell heparanase inhibitor, was accomplished. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.004

文献信息

• Asymmetric synthesis of (+)-trachyspic acid
  作者：Kenji Morokuma、Yuko Taira、Yumiko Uehara、Setsuya Shibahara、Keisuke Takahashi、Jun Ishihara、Susumi Hatakeyama

  DOI：10.1016/j.tetlet.2008.07.004

  日期：2008.10

  Aldol reaction of di-tert-butyl 4-(4-methoxybenzyloxy)-2-oxobutanoate with pent-4-enal using (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea hydrochloride as a catalyst, followed by Pinnick oxidation and tert-butyl esterification, gave (2S,3S)-di-tert-butyl 2-(2-(4-methoxybenzyloxy)ethyl)-3-allyl-2-hydroxysuccinate in high optical purity (85% ee), from which the total synthesis of (+)-trachyspic acid, a tumor cell heparanase inhibitor, was accomplished. (C) 2008 Elsevier Ltd. All rights reserved.