Fmoc-NMeIle-Thr-OMe | 220663-37-6

• 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: Fmoc-NMeIle-Thr-OMe
• 英文别名: Fmoc-N(Me)Ile-Thr-OMe；methyl (2S,3R)-2-[[(2S,3S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-methylpentanoyl]amino]-3-hydroxybutanoate
• CAS: 220663-37-6
• 化学式: C₂₇H₃₄N₂O₆
• 分子量: 482.577
• InChiKey: ZNYZFWSOAILQKC-OOADCZFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Fmoc-NMeIle-Thr-OMe 在 lithium hydroxide 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 10.0h， 生成 <2-C(S)>-Fmoc-NMeIle-Thr(Ψ^H,pmppro)-OH
  参考文献：
  名称：

  Stereocontrol during the formation of 2-C mono-arylated pseudo-prolines by aromatic stacking interaction

  摘要：

  When treated with anisaldehyde dimethylacetal the O-benzyl ester protected dipeptide Fmoc-NMeIle-Thr-OBzl (2, cf. Scheme 3), cyclizes to the 2-C(S) epimer 3b assigned by NMR spectroscopy to chirality (R) at the 2-C position of the resulting substituted 1,3-oxazolidine (Psi Pro) unit, while in the acetalization of the corresponding O-methylester Fmoc-NMeIle-Thr-OMe (6),the 2-C(S) epimer 7a is predominantly formed stereoselectively and in quantitative yield. The course of the reaction can be rationalized by aromatic stacking interactions involving the benzyl ester and aryl ether groups in a transition state close to a product structure of(R) chirality, whereas the lack of such interactions in the case of the methyl ester can be used to direct the acetalization towards the 2-C(S) epimer. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01039-4
• 作为产物：
  描述：

  N-甲基-L-异亮氨酸 在 N-甲基吗啉 、 五氟苯酚 、 sodium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 23.0h， 生成 Fmoc-NMeIle-Thr-OMe
  参考文献：
  名称：

  Stereocontrol during the formation of 2-C mono-arylated pseudo-prolines by aromatic stacking interaction

  摘要：

  When treated with anisaldehyde dimethylacetal the O-benzyl ester protected dipeptide Fmoc-NMeIle-Thr-OBzl (2, cf. Scheme 3), cyclizes to the 2-C(S) epimer 3b assigned by NMR spectroscopy to chirality (R) at the 2-C position of the resulting substituted 1,3-oxazolidine (Psi Pro) unit, while in the acetalization of the corresponding O-methylester Fmoc-NMeIle-Thr-OMe (6),the 2-C(S) epimer 7a is predominantly formed stereoselectively and in quantitative yield. The course of the reaction can be rationalized by aromatic stacking interactions involving the benzyl ester and aryl ether groups in a transition state close to a product structure of(R) chirality, whereas the lack of such interactions in the case of the methyl ester can be used to direct the acetalization towards the 2-C(S) epimer. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01039-4

文献信息

• Configurational and Conformational Control on Formation and Oligomerization of 2-C Mono-Arylated Pseudo-Proline Dipeptide Building Units by Aromatic Stacking Interactions
  作者：Michael Keller、Manfred Mutter、Christian Lehmann

  DOI：10.1055/s-0031-1289595

  日期：——

  under the same proton catalyzed cyclization conditions. With boron trifluoride etherate as Lewis acid the reaction is particularly fast and leads selectively to the prolyl threonine derived 2-C(R) dipeptide building block 8b, which could conveniently be assembled into a nonamer with a virtually solvent independent CD-spectrum of the polyproline type I (cis amide bonds).

  已观察到 O-苄基二肽酯 Fmoc-NMeIle-Thr-OBn (1) 和 Fmoc-Pro-Thr-OBn (6) 的亲电诱导环状缩醛形成主要导致 (R) 非对映异构体 2b 和 8b 在得到的取代的 Id-恶唑烷 (Psi Pro) 单元的 2-C 位置，而在相应的 O-甲酯 4 缩醛化后，2-C(S) 差向异构体 5a 主要在相同的质子催化环化条件下形成。使用三氟化硼醚合物作为路易斯酸，反应特别快，并选择性地导致脯氨酰苏氨酸衍生的 2-C(R) 二肽结构单元 8b，它可以方便地组装成具有几乎不依赖溶剂的聚脯氨酸 CD 谱的九聚体I型（顺式酰胺键）。
• Stereocontrol during the formation of 2-C mono-arylated pseudo-prolines by aromatic stacking interaction
  作者：Michael Keller、Christian Lehmann、Manfred Mutter

  DOI：10.1016/s0040-4020(98)01039-4

  日期：1999.1

  When treated with anisaldehyde dimethylacetal the O-benzyl ester protected dipeptide Fmoc-NMeIle-Thr-OBzl (2, cf. Scheme 3), cyclizes to the 2-C(S) epimer 3b assigned by NMR spectroscopy to chirality (R) at the 2-C position of the resulting substituted 1,3-oxazolidine (Psi Pro) unit, while in the acetalization of the corresponding O-methylester Fmoc-NMeIle-Thr-OMe (6),the 2-C(S) epimer 7a is predominantly formed stereoselectively and in quantitative yield. The course of the reaction can be rationalized by aromatic stacking interactions involving the benzyl ester and aryl ether groups in a transition state close to a product structure of(R) chirality, whereas the lack of such interactions in the case of the methyl ester can be used to direct the acetalization towards the 2-C(S) epimer. (C) 1998 Elsevier Science Ltd. All rights reserved.