methyl (S)-2-[((2S,4R)-4-hydroxy-1-(pyridin-4-yl)pyrrolidine-2-carbonyl)amino]-3-(1H-indol-3-yl)propanoate | 533914-96-4

• 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: methyl (S)-2-[((2S,4R)-4-hydroxy-1-(pyridin-4-yl)pyrrolidine-2-carbonyl)amino]-3-(1H-indol-3-yl)propanoate
• 英文别名: pyrid-4-yl-Hyp-Trp-OMe；methyl (2S)-2-[[(2S,4R)-4-hydroxy-1-pyridin-4-ylpyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoate
• CAS: 533914-96-4
• 化学式: C₂₂H₂₄N₄O₄
• 分子量: 408.457
• InChiKey: AUBRGGWNHUVAKF-UXPWSPDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-BOC-N-IM-1-甲基-L-组氨酸 、 methyl (S)-2-[((2S,4R)-4-hydroxy-1-(pyridin-4-yl)pyrrolidine-2-carbonyl)amino]-3-(1H-indol-3-yl)propanoate 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以92%的产率得到
  参考文献：
  名称：

  Preparation and properties of chiral 4-pyrrolidinopyridine (PPY) analogues with dual functional side chains

  摘要：

  Chiral 4-pyrrolidinopyridine analogues 8-13 with two distinct functional side chains at C(2) and C(4) of the pyrrolidine ring were prepared from 4-hydroxy-L-proline. We examined desymmetrization of meso-1,3-cyclohexanediol through enantioselective acylation using these catalysts and found that introduction of a C(4)-side chain was effective for improving both the chemo- and enantioselectivity of acylation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00021-2
• 作为产物：
  描述：

  Hyp(Ot-Bu)Ot-Bu 在 N-甲基吗啉 、 碘代三甲硅烷 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成 methyl (S)-2-[((2S,4R)-4-hydroxy-1-(pyridin-4-yl)pyrrolidine-2-carbonyl)amino]-3-(1H-indol-3-yl)propanoate
  参考文献：
  名称：

  Preparation and properties of chiral 4-pyrrolidinopyridine (PPY) analogues with dual functional side chains

  摘要：

  Chiral 4-pyrrolidinopyridine analogues 8-13 with two distinct functional side chains at C(2) and C(4) of the pyrrolidine ring were prepared from 4-hydroxy-L-proline. We examined desymmetrization of meso-1,3-cyclohexanediol through enantioselective acylation using these catalysts and found that introduction of a C(4)-side chain was effective for improving both the chemo- and enantioselectivity of acylation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00021-2

文献信息

• Regioselective Acylation of Octyl β-<scp>d</scp>-Glucopyranoside by Chiral 4-Pyrrolidinopyridine Analogues
  作者：Takeo Kawabata、Wataru Muramatsu、Tadashi Nishio、Takeshi Shibata、Yoshiharu Uruno、Roland Stragies

  DOI：10.1055/s-2008-1032176

  日期：2008.3

  D-glucopyranoside with isobutyric anhydride in the presence of the catalysts gave the 6- O-acylate as the major product via acylation of a primary hydroxyl group. On the other hand, the 4- O-acylate was obtained as the major product in 66% regioselectivity via acylation of the secondary hydroxyl group at C-4 on treatment of octyl β- D-glucopyranoside with isobutyric anhydride in the presence of a PPY catalyst. Use

  已经从 TRANS-4-羟基-L-脯氨酸制备了具有由吲哚单元组成的双功能侧链的手性 4-吡咯烷基吡啶 (PPY) 类似物。在催化剂存在下用异丁酸酐处理辛基β-D-吡喃葡萄糖苷通过伯羟基的酰化得到6-O-酰化物作为主要产物。另一方面，在 PPY 存在下，用异丁酸酐处理辛基 β-D-吡喃葡萄糖苷，通过 C-4 处仲羟基的酰化，获得 66% 区域选择性的主要产物 4-O-酰化物。催化剂。在催化剂存在下使用异丁酰氯代替异丁酸酐得到87％区域选择性的6-O-酰化物。
• Preparation and properties of chiral 4-pyrrolidinopyridine (PPY) analogues with dual functional side chains
  作者：Takeo Kawabata、Roland Stragies、Takayuki Fukaya、Yoshie Nagaoka、Hartmut Schedel、Kaoru Fuji

  DOI：10.1016/s0040-4039(03)00021-2

  日期：2003.2

  Chiral 4-pyrrolidinopyridine analogues 8-13 with two distinct functional side chains at C(2) and C(4) of the pyrrolidine ring were prepared from 4-hydroxy-L-proline. We examined desymmetrization of meso-1,3-cyclohexanediol through enantioselective acylation using these catalysts and found that introduction of a C(4)-side chain was effective for improving both the chemo- and enantioselectivity of acylation. (C) 2003 Elsevier Science Ltd. All rights reserved.