methyl (2E,4R,5R)-4-<(tert-butoxycarbonyl)amino>-5-hydroxy-2-hexenoate acetonide | 146778-87-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (2E,4R,5R)-4-<(tert-butoxycarbonyl)amino>-5-hydroxy-2-hexenoate acetonide
• 英文别名: (4S,5R)-2,2,5-trimethyl-3-(tert-butoxycarbonyl)-4-(E-methoxycarbonylethenyl)-oxazolidine；(4R,5R,E)-tert-butyl 4-(3-methoxy-3-oxoprop-1-enyl)-2,2,5-trimethyloxazolidine-3-carboxylate；tert-butyl (4R,5R)-4-[(E)-3-methoxy-3-oxoprop-1-enyl]-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 146778-87-2
• 化学式: C₁₅H₂₅NO₅
• 分子量: 299.367
• InChiKey: AYIVSUXAFDWOLW-WUNNSPOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2E,4R,5R)-4-<(tert-butoxycarbonyl)amino>-5-hydroxy-2-hexenoate acetonide 在 palladium on activated charcoal 氢气 、 二异丁基氢化铝 、 溶剂黄146 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 145.08h， 生成 2,3,4,6-tetradeoxy-4-(N-tert-butoxycarbonyl)amino-β-D-galactopyranoside
  参考文献：
  名称：

  A new access to enantiomerically pure deoxy aminohexoses: Methyl 4-amino-4,6-dideoxygulopyranoside and epi-tolyposamine

  摘要：

  New efficient synthetic routes have been developed starting from the fully protected L-threonine derivative 1 for some deoxy-4-aminohexoses: methyl 4-amino-4,6-dideoxy gulopyranoside 2 and epi-tolyposamine 3. The title compounds were synthesized using an improved Horner-Emmons reaction of the threonine derived aldehyde 7. A new method for selective removal of the aminal protection is also reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00304-9
• 作为产物：
  描述：

  BOC-苏氨酸甲酯 在 18-冠醚-6 、 三氟化硼乙醚 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.41h， 生成 methyl (2E,4R,5R)-4-<(tert-butoxycarbonyl)amino>-5-hydroxy-2-hexenoate acetonide
  参考文献：
  名称：

  A new access to enantiomerically pure deoxy aminohexoses: Methyl 4-amino-4,6-dideoxygulopyranoside and epi-tolyposamine

  摘要：

  New efficient synthetic routes have been developed starting from the fully protected L-threonine derivative 1 for some deoxy-4-aminohexoses: methyl 4-amino-4,6-dideoxy gulopyranoside 2 and epi-tolyposamine 3. The title compounds were synthesized using an improved Horner-Emmons reaction of the threonine derived aldehyde 7. A new method for selective removal of the aminal protection is also reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00304-9

文献信息

• SYNTHESIS OF FR901464 AND ANALOGS WITH ANTITUMOR ACTIVITY
  申请人：KOIDE Kazunori

  公开号：US20080096879A1

  公开（公告）日：2008-04-24

  The present invention provides novel analogs of FR901464, as well as an improved methodology for preparing FR901464 and its analogs. These compounds display an anti-cancer activity and are candidates for therapies against a number of disease states associated with dysfunctional RNA splicing.

  本发明提供了FR901464的新颖类似物，以及制备FR901464及其类似物的改进方法。这些化合物显示出抗癌活性，并可作为治疗与RNA剪接功能障碍相关的一系列疾病状态的候选药物。
• [EN] FR901464 AND ANALOGS WITH ANTITUMOR ACTIVITY AND METHOD FOR THEIR PREPARATION<br/>[FR] FR901464 ET ANALOGUES PRÉSENTANT UNE ACTIVITÉ ANTITUMORALE, ET PROCÉDÉ DE PRÉPARATION DE CES COMPOSÉS
  申请人：UNIV PITTSBURGH

  公开号：WO2009031999A1

  公开（公告）日：2009-03-12

  The present invention provides analogs of FR901464, as well as a methodology for preparing FR901464 and its analogs. These compounds display an anti-cancer activity and are candidates for therapies against a number of disease states associated with dysfunctional RNA splicing.

  本发明提供了FR901464的类似物，以及制备FR901464及其类似物的方法。这些化合物显示出抗肿瘤活性，并且是针对与RNA剪接功能异常相关联的多种疾病状态治疗的候选物。
• Reductive cleavage reaction of .gamma.-functionalized .alpha.,.beta.-unsaturated esters and halomethyls mediated with magnesium in methanol
  作者：Chwang Siek Pak、Eun Lee、Ge Hyeong Lee

  DOI：10.1021/jo00058a038

  日期：1993.3

  Reductive cleavage of various types of C-O and C-N bonds tethered to alpha,beta-unsaturated esters and halomethyls was mediated with magnesium in methanol, which provided a facile method for the synthesis of delta-hydroxy or delta-amino beta,gamma-unsaturated esters and allylic alcohols. Regardless of the geometry (E or Z) of the alpha,beta-unsaturated esters, 1a-b, 5a-c, 11, 13, and 23, the cleavage product obtained was exclusively the E isomer of the corresponding deconjugated hydroxy and amino esters. The steric bias and ring strain of 15, 17, and 21 gave rise to a product mixture of E and Z isomers.
• Pak Chwang Siek, Lee Eun, Lee Ge Hyeong, J. Org. Chem, 58 (1993) N 6, S 1523-1530
  作者：Pak Chwang Siek, Lee Eun, Lee Ge Hyeong

  DOI：——

  日期：——
• US7825267B2
  申请人：——

  公开号：US7825267B2

  公开（公告）日：2010-11-02