(R)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)butanoic acid | 1135148-98-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (R)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)butanoic acid
• 英文别名: Fmoc-β³hSer(All)-OH；N-Fmoc-O-allyl-L-β-homoserine；Fmoc-O-allyl-β-serine；(3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-prop-2-enoxybutanoic acid
• CAS: 1135148-98-9
• 化学式: C₂₂H₂₃NO₅
• 分子量: 381.428
• InChiKey: XFIIMIWJXLZBEJ-OAHLLOKOSA-N

物化性质

• 熔点：
  69-71 °C
• 沸点：
  610.7±55.0 °C(predicted)
• 密度：
  1.229±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)butanoic acid 、 Fmoc-L-beta-高缬氨酸 、 9-芴甲氧羰基-L-beta-高丙氨酸 、 (R)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methyl-hexanoic acid 、 芴甲氧羰基-L-β-高亮氨酸 在 N,N'-二异丙基碳二亚胺 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成
  参考文献：
  名称：

  Synthesis of Stapled β³-Peptides through Ring-Closing Metathesis

  摘要：

  The first synthesis of carbon-stapled beta(3)-peptides is reported. The precursor beta(3)-peptides, with -allyl beta-serines located in an i/i+3 relationship, were prepared on solid phase. We show that efficient ring-closing metathesis (RCM) of these new beta(3)-peptides proceeds smoothly either in solution or on an appropriate solid support. All products were generated with high selectivity for the E-isomer.

  DOI：

  10.1021/ol901803d
• 作为产物：
  描述：

  (2R)-1-carboxy-3-(prop-2-en-1-yloxy)propan-2-aminium trifluoroacetate 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 sodium carbonate 作用下， 以 丙酮 为溶剂， 以96%的产率得到(R)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)butanoic acid
  参考文献：
  名称：

  The synthesis of Fmoc-O-allyl β-serine

  摘要：

  Two concise routes for the synthesis of the title amino acid have been developed. The first route employs Seebach's general approach [Seebach, D.; Lelais, G.; Micuch, P.; Josien-Lefebvre, D.; Rossi, F. Helv. Chim. Acta 2004, 87, 3131] with Arndt Eistert homologation of Boc-alpha-allyl alpha-serine as the key process. The second route employs an approach using Boc-alpha-aspartic acid as a starting material [Salzmann, T.N.; Ratcliffe, R.W.; Christensen, B.G.; Bouffard, F.A.J Am. Chem. Soc. 1980, 102, 6163; Rodriguez, M.; Llinares, M.; Doulut, S.; Heitz, A.; Martinez, J. Tetrahedron. Lett. 1991, 32, 923] with a selective palladium-catalysed O-allylation [Haight, A.R: Stoner, EJ.; Peterson, MJ.: Grover, V.K.J. Org. Chem. 2003, 68, 8092] as key processes. These two routes are evaluated for their relative efficiency and safety. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.022

文献信息

• Synthesis and High-Resolution NMR Structure of a β3-Octapeptide with and without a Tether Introduced by Olefin Metathesis
  作者：Marc-Olivier Ebert、James Gardiner、Steven Ballet、Andrew D. Abell、Dieter Seebach

  DOI：10.1002/hlca.200900311

  日期：2009.12

  in CD3OH of the two β3‐octapeptide derivatives without (i.e., 1) and with tether (i.e., 4; Tables 1–6, and Figs. 4 and 5) provided structures of a degree of precision (by including the complete set of side chain–side chain and side chain–backbone NOEs) which is unrivaled in β‐peptide NMR‐solution‐structure determination. Comparison of the two structures (Fig. 5) reveals small differences in side‐chain

  之间桥接（我） -和（我3）位上的β 3 -肽具有适当长度的系链，是为了防止相应的3 14螺旋从展开（图1）。所述β 3 -肽H- β 3 hVal- β 3 hLys- β 3 hSer（全部） - β 3 hPhe- β 3 hGlu- β 3 hSer（全部） - β 3 hTyr- β 3 HILE-OH（1 ;具有烯丙基化的β在3-位和6-位hSer残基），和三个系绳β -肽2 - 4（与1通过闭环复分解）已合成（固相耦合，Fmoc策略，在氯三苯甲基树脂;方案）。拴系的比较分析CD β -肽4和它的非栓系类似物1表明螺旋倾向是由（CH显著增强（三倍CD强度）2）4之间的接头β 3 hSer侧链（图2） 。这个结论是基于这样的前提，即负数的强度棉附近的CD光谱215nm处效果β 3 -肽代表了“螺旋含量”的量度。NMR分析在CD 3两者的OH β 3而不-octapeptide衍生物（即，1），并用系绳（即，4
• The synthesis of Fmoc-O-allyl β-serine
  作者：Ylva Bergman、Marisa Ciampini、Sania Jalal、Helen Rachel Lagiakos、Marie-Isabel Aguilar、Patrick Perlmutter

  DOI：10.1016/j.tetasy.2008.12.022

  日期：2008.12

  Two concise routes for the synthesis of the title amino acid have been developed. The first route employs Seebach's general approach [Seebach, D.; Lelais, G.; Micuch, P.; Josien-Lefebvre, D.; Rossi, F. Helv. Chim. Acta 2004, 87, 3131] with Arndt Eistert homologation of Boc-alpha-allyl alpha-serine as the key process. The second route employs an approach using Boc-alpha-aspartic acid as a starting material [Salzmann, T.N.; Ratcliffe, R.W.; Christensen, B.G.; Bouffard, F.A.J Am. Chem. Soc. 1980, 102, 6163; Rodriguez, M.; Llinares, M.; Doulut, S.; Heitz, A.; Martinez, J. Tetrahedron. Lett. 1991, 32, 923] with a selective palladium-catalysed O-allylation [Haight, A.R: Stoner, EJ.; Peterson, MJ.: Grover, V.K.J. Org. Chem. 2003, 68, 8092] as key processes. These two routes are evaluated for their relative efficiency and safety. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of Stapled β³-Peptides through Ring-Closing Metathesis
  作者：Ylva E. Bergman、Mark P. Del Borgo、Romila D. Gopalan、Sania Jalal、Sharon E. Unabia、Marisa Ciampini、Daniel J. Clayton、Jordan M. Fletcher、Roger J. Mulder、Jacqueline A. Wilce、Marie-Isabel Aguilar、Patrick Perlmutter

  DOI：10.1021/ol901803d

  日期：2009.10.1

  The first synthesis of carbon-stapled beta(3)-peptides is reported. The precursor beta(3)-peptides, with -allyl beta-serines located in an i/i+3 relationship, were prepared on solid phase. We show that efficient ring-closing metathesis (RCM) of these new beta(3)-peptides proceeds smoothly either in solution or on an appropriate solid support. All products were generated with high selectivity for the E-isomer.