(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-(2-pentadecyl-[1,3]dioxolan-2-yl)-butanoic acid | 1114400-76-8

• 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: (S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-(2-pentadecyl-[1,3]dioxolan-2-yl)-butanoic acid
• 英文别名: Fmoc-Pdiob-OH；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-(2-pentadecyl-1,3-dioxolan-2-yl)butanoic acid
• CAS: 1114400-76-8
• 化学式: C₃₇H₅₃NO₆
• 分子量: 607.831
• InChiKey: HBCNFYMBFJAFTE-UMSFTDKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  44
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Fmoc-cysteine-(S-farnesyl) resin 、 (S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-(2-pentadecyl-[1,3]dioxolan-2-yl)-butanoic acid 、 Fmoc-甘氨酸 、 FMOC-O-叔丁基-L-丝氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 Fmoc-L-蛋氨酸 在 哌啶 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.13h， 以38 mg的产率得到C₇₃H₁₃₂N₈O₁₁S₂
  参考文献：
  名称：

  Synthesis and application in SPPS of a stable amino acid isostere of palmitoyl cysteine

  摘要：

  (S)-2-Amino-4-(2-pentadecyl-1,3-dioxolan-2-yl)-butanoic acid, 11, Pdiob, a synthetic analogue C-isostere of palmitoylated cysteine, has been prepared starting from tetrabenzyl glutamic acid. The less hindered benzyl carboxylate ester was transformed into the corresponding beta-ketophosphonate and subjected to a Horner-Wadsworth-Emmons reaction followed by hydrogenation/hydrogenolysis. This product was used for the preparation on solid phase and under microwave dielectric heating of a highly lipidated peptide that can be considered as an acid stable analogue of the C-terminus of the H-Ras heptapeptides 180-186. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.033
• 作为产物：
  描述：

  (S)-2-amino-4-(2-pentadecyl-[1,3]dioxolan-2-yl)-butanoic acid 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 三乙胺 、 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以95%的产率得到(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-(2-pentadecyl-[1,3]dioxolan-2-yl)-butanoic acid
  参考文献：
  名称：

  Synthesis and application in SPPS of a stable amino acid isostere of palmitoyl cysteine

  摘要：

  (S)-2-Amino-4-(2-pentadecyl-1,3-dioxolan-2-yl)-butanoic acid, 11, Pdiob, a synthetic analogue C-isostere of palmitoylated cysteine, has been prepared starting from tetrabenzyl glutamic acid. The less hindered benzyl carboxylate ester was transformed into the corresponding beta-ketophosphonate and subjected to a Horner-Wadsworth-Emmons reaction followed by hydrogenation/hydrogenolysis. This product was used for the preparation on solid phase and under microwave dielectric heating of a highly lipidated peptide that can be considered as an acid stable analogue of the C-terminus of the H-Ras heptapeptides 180-186. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.033

文献信息

• Synthesis and application in SPPS of a stable amino acid isostere of palmitoyl cysteine
  作者：Elena Cini、Lucia Raffaella Lampariello、Manuela Rodriquez、Maurizio Taddei

  DOI：10.1016/j.tet.2008.11.033

  日期：2009.1

  (S)-2-Amino-4-(2-pentadecyl-1,3-dioxolan-2-yl)-butanoic acid, 11, Pdiob, a synthetic analogue C-isostere of palmitoylated cysteine, has been prepared starting from tetrabenzyl glutamic acid. The less hindered benzyl carboxylate ester was transformed into the corresponding beta-ketophosphonate and subjected to a Horner-Wadsworth-Emmons reaction followed by hydrogenation/hydrogenolysis. This product was used for the preparation on solid phase and under microwave dielectric heating of a highly lipidated peptide that can be considered as an acid stable analogue of the C-terminus of the H-Ras heptapeptides 180-186. (C) 2008 Elsevier Ltd. All rights reserved.