(S)-2-Benzyloxycarbonylamino-3-[6-((S)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-pyridin-2-yl]-propionic acid methyl ester | 177977-57-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-Benzyloxycarbonylamino-3-[6-((S)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-pyridin-2-yl]-propionic acid methyl ester
• 英文别名: methyl (2S)-3-[6-[(2S)-3-methoxy-3-oxo-2-(phenylmethoxycarbonylamino)propyl]pyridin-2-yl]-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 177977-57-0
• 化学式: C₂₉H₃₁N₃O₈
• 分子量: 549.58
• InChiKey: ZTNYOQKLXDWMBJ-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-2-Benzyloxycarbonylamino-3-[6-((S)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-pyridin-2-yl]-propionic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以90%的产率得到(S)-2-Amino-3-[6-((S)-2-amino-2-methoxycarbonyl-ethyl)-pyridin-2-yl]-propionic acid methyl ester
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Bis-armed Aromatic Amino Acid Derivatives. Problems Related to the Synthesis of Enantiomerically Pure Bis-methyl Ester of the (S,S)-Pyridine-2,6-diyl Bis-alanine.

  摘要：

  (S,S)-Pyridine-2,6-diyl bis-alanines 8 and 9 carrying protecting groups suitable for peptide synthesis have been synthesised Rom 2,6-pyridinedicarbaldehyde by the phosphonoglycine condensation route followed by catalytic by hydrogenation with Rh{(COD)[(R,R)-DIPAMP]}BF4. The alternative route via double Heck coupling of 2,6-dibromopyridine and benzyl Boc-amidoacrylate was unsuccessful although mono-coupling could be achieved. The reasons for this failure are discussed as well as the failure of two mono-armed didehydroamino acid derivatives to undergo hydrogenation with Rh-bisphosphine catalysts. The CuCl2 and RhCl3 complexes of the bis-amino derivative 9 were prepared; a 20% e.e. was achieved in the cyclopropanation of styrene with ethyl diazoacetate using the Cu(II)-complex as a catalyst.

  DOI：

  10.3891/acta.chem.scand.50-0316
• 作为产物：
  描述：

  (±)-Z-α-膦酰甘氨酸三甲酯 在 [Rh((R,R)-DIPAMP)(COD)]BF₄ 1,1,2,3-四甲基胍 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 45.0 ℃ 、448.16 kPa 条件下， 反应 64.0h， 生成 (S)-2-Benzyloxycarbonylamino-3-[6-((S)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-pyridin-2-yl]-propionic acid methyl ester
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Bis-armed Aromatic Amino Acid Derivatives. Problems Related to the Synthesis of Enantiomerically Pure Bis-methyl Ester of the (S,S)-Pyridine-2,6-diyl Bis-alanine.

  摘要：

  (S,S)-Pyridine-2,6-diyl bis-alanines 8 and 9 carrying protecting groups suitable for peptide synthesis have been synthesised Rom 2,6-pyridinedicarbaldehyde by the phosphonoglycine condensation route followed by catalytic by hydrogenation with Rh{(COD)[(R,R)-DIPAMP]}BF4. The alternative route via double Heck coupling of 2,6-dibromopyridine and benzyl Boc-amidoacrylate was unsuccessful although mono-coupling could be achieved. The reasons for this failure are discussed as well as the failure of two mono-armed didehydroamino acid derivatives to undergo hydrogenation with Rh-bisphosphine catalysts. The CuCl2 and RhCl3 complexes of the bis-amino derivative 9 were prepared; a 20% e.e. was achieved in the cyclopropanation of styrene with ethyl diazoacetate using the Cu(II)-complex as a catalyst.

  DOI：

  10.3891/acta.chem.scand.50-0316

文献信息

• Preparation of (S)-2-quinolylalanine by asymmetric hydrogenation
  作者：Stephen W. Jones、Christopher F. Palmer、Jane M. Paul、Peter D. Tiffin

  DOI：10.1016/s0040-4039(98)02568-4

  日期：1999.2

  The synthesis of (S)-2-quinolylalanine through asymmetric hydrogenation with (S,S)-Et-DuPHOS-Rh is described. The reaction has been extended to other 2-pyridylalanie derivatives.

  描述了通过与（S，S）-Et-DuPHOS-Rh的不对称氢化来合成（S）-2-喹啉基丙氨酸。该反应已扩展至其他2-吡啶基丙氨酸衍生物。
• Catalytic Asymmetric Synthesis of Bis-armed Aromatic Amino Acid Derivatives. Problems Related to the Synthesis of Enantiomerically Pure Bis-methyl Ester of the (S,S)-Pyridine-2,6-diyl Bis-alanine.
  作者：B. Basu、T. Frejd、Klaus Harms、Kim Simonsen、György Liptay、Katrin Trautwein-Fritz、Joseph Stackhouse、Mauro I. Ciglic、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0316

  日期：——

  (S,S)-Pyridine-2,6-diyl bis-alanines 8 and 9 carrying protecting groups suitable for peptide synthesis have been synthesised Rom 2,6-pyridinedicarbaldehyde by the phosphonoglycine condensation route followed by catalytic by hydrogenation with Rh(COD)[(R,R)-DIPAMP]}BF4. The alternative route via double Heck coupling of 2,6-dibromopyridine and benzyl Boc-amidoacrylate was unsuccessful although mono-coupling could be achieved. The reasons for this failure are discussed as well as the failure of two mono-armed didehydroamino acid derivatives to undergo hydrogenation with Rh-bisphosphine catalysts. The CuCl2 and RhCl3 complexes of the bis-amino derivative 9 were prepared; a 20% e.e. was achieved in the cyclopropanation of styrene with ethyl diazoacetate using the Cu(II)-complex as a catalyst.