ditert-butyl (2S,3S)-3-[4-(1,3-dioxolan-2-yl)-3-methylidene-2-oxotridecyl]-2-hydroxy-2-[2-[(4-methoxyphenyl)methoxy]ethyl]butanedioate | 1073862-10-8

• 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,3S)-3-[4-(1,3-dioxolan-2-yl)-3-methylidene-2-oxotridecyl]-2-hydroxy-2-[2-[(4-methoxyphenyl)methoxy]ethyl]butanedioate
• CAS: 1073862-10-8
• 化学式: C₃₉H₆₂O₁₀
• 分子量: 690.915
• InChiKey: JJIDOSPTUWZLCM-DZTBYMKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  49
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ditert-butyl (2S,3S)-3-[4-(1,3-dioxolan-2-yl)-3-methylidene-2-oxotridecyl]-2-hydroxy-2-[2-[(4-methoxyphenyl)methoxy]ethyl]butanedioate 在 高氯酸 作用下， 以 四氢呋喃 为溶剂， 生成 ditert-butyl (2S,3S,5R)-7-hydroxy-2-[2-[(4-methoxyphenyl)methoxy]ethyl]-9-methylidene-8-nonyl-1,6-dioxaspiro[4.4]nonane-2,3-dicarboxylate 、
  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
• 作为产物：
  描述：

  (2RS,3RS)-3-[3-(1-[1,3]dioxolan-2-yldecyl)-2-oxobut-3-enyl]-2-[2-(4-methoxybenzyloxy)ethyl]-2-(trimethylsilanyloxy)succinic acid di-tert-butyl ester 在 吡啶 、 氢氟酸 、 水 作用下， 以 乙腈 为溶剂， 生成 ditert-butyl (2S,3S)-3-[4-(1,3-dioxolan-2-yl)-3-methylidene-2-oxotridecyl]-2-hydroxy-2-[2-[(4-methoxyphenyl)methoxy]ethyl]butanedioate
  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