N^α-Fmoc-(2R,3R)-O-benzyl-β-methoxytyrosine | 910056-49-4

• 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: N^α-Fmoc-(2R,3R)-O-benzyl-β-methoxytyrosine
• 英文别名: (2R,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methoxy-3-(4-phenylmethoxyphenyl)propanoic acid
• CAS: 910056-49-4
• 化学式: C₃₂H₂₉NO₆
• 分子量: 523.585
• InChiKey: VZMOTBPYXFANKL-LOYHVIPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  N^α-Fmoc-(2R,3R)-O-benzyl-β-methoxytyrosine 、 Fmoc-L-亮氨酸 、 Fmoc-Thr-OH 、 FMOC-N-甲基-L-丙氨酸 以20%的产率得到(S)-2-{[(2R,3R)-2-[(S)-2-({(S)-2-[(R)-2-((2S,3R)-2-Amino-3-hydroxy-butyrylamino)-5-guanidino-pentanoylamino]-4-methyl-pentanoyl}-methyl-amino)-4-carbamoyl-butyrylamino]-3-(4-hydroxy-phenyl)-3-methoxy-propionyl]-methyl-amino}-propionic acid
  参考文献：
  名称：

  Solid-Phase Synthesis and Configurational Reassigment of Callipeltin E. Implications for the Structures of Callipeltins A and B

  摘要：

  Two possible isomers of the natural product callipeltin E (1, 5) were synthesized by using an Fmoc-based solid-phase strategy in 7 steps, in 20% and 26% overall yields, respectively. The H-1 NMR spectrum of synthetic 5 correlated closely with that of the natural product, whereas that of 1 did not, providing confirmation of the configurational reassignment of the N-terminal residue of callipeltin E as D-allothreonine. This result strongly implies that the corresponding residue in the closely related cyclic depsipeptides callipeltins A and B should also be considered a D-allothreonine residue.

  DOI：

  10.1021/jo060351h
• 作为产物：
  描述：

  N^α-Fmoc-(2R,3R)-O-benzyl-β-methoxytyrosine allyl ester 在 三乙基硅烷 、 四(三苯基膦)钯 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以81%的产率得到N^α-Fmoc-(2R,3R)-O-benzyl-β-methoxytyrosine
  参考文献：
  名称：

  Solid-Phase Synthesis and Configurational Reassigment of Callipeltin E. Implications for the Structures of Callipeltins A and B

  摘要：

  Two possible isomers of the natural product callipeltin E (1, 5) were synthesized by using an Fmoc-based solid-phase strategy in 7 steps, in 20% and 26% overall yields, respectively. The H-1 NMR spectrum of synthetic 5 correlated closely with that of the natural product, whereas that of 1 did not, providing confirmation of the configurational reassignment of the N-terminal residue of callipeltin E as D-allothreonine. This result strongly implies that the corresponding residue in the closely related cyclic depsipeptides callipeltins A and B should also be considered a D-allothreonine residue.

  DOI：

  10.1021/jo060351h

文献信息

• Solid-Phase Synthesis and Configurational Reassigment of Callipeltin E. Implications for the Structures of Callipeltins A and B
  作者：Selçuk Çalimsiz、Ángel I. Morales Ramos、Mark A. Lipton

  DOI：10.1021/jo060351h

  日期：2006.8.1

  Two possible isomers of the natural product callipeltin E (1, 5) were synthesized by using an Fmoc-based solid-phase strategy in 7 steps, in 20% and 26% overall yields, respectively. The H-1 NMR spectrum of synthetic 5 correlated closely with that of the natural product, whereas that of 1 did not, providing confirmation of the configurational reassignment of the N-terminal residue of callipeltin E as D-allothreonine. This result strongly implies that the corresponding residue in the closely related cyclic depsipeptides callipeltins A and B should also be considered a D-allothreonine residue.