N-Cbz-4-methoxy-3-(methoxylmethyl)-L-phenylalanine methyl ester | 1219720-76-9

• 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-Cbz-4-methoxy-3-(methoxylmethyl)-L-phenylalanine methyl ester
• 英文别名: methyl (2S)-3-[4-methoxy-3-(methoxymethyl)phenyl]-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 1219720-76-9
• 化学式: C₂₁H₂₅NO₆
• 分子量: 387.433
• InChiKey: CCRPELDOOYXYET-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-Cbz-4-methoxy-3-(methoxylmethyl)-L-phenylalanine methyl ester 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以97%的产率得到N-CBZ-3-甲基-4-甲氧基-L-苯丙氨酸甲酯
  参考文献：
  名称：

  A new approach to the synthesis of l-3-hydroxy-4-methoxy-5-methyl-phenylalanine derivatives from l-tyrosine

  摘要：

  A practical procedure to regioselectively install a methyl group and a phenolic hydroxyl group onto L-tyrosine was developed. By using this approach, protected L-3-hydroxy-4-methoxy-5-methyl-phenylalanine and L-3-hydroxy-4-methoxy-5-methyl-phenylalanol, which are utilized in efficient syntheses of the relevant tetrahydroisoquinoline alkaloids, were prepared conveniently with high yield (c) 2010 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.024
• 作为产物：
  描述：

  硫酸二甲酯 、 (S)-N-benzyloxycarbonyl-4-hydroxy-3-hydroxymethylphenylalanine 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 N-Cbz-4-methoxy-3-(methoxylmethyl)-L-phenylalanine methyl ester 、 N-Cbz-3-hydroxymethyl-4-methoxy-L-phenylalanine methyl ester
  参考文献：
  名称：

  A new approach to the synthesis of l-3-hydroxy-4-methoxy-5-methyl-phenylalanine derivatives from l-tyrosine

  摘要：

  A practical procedure to regioselectively install a methyl group and a phenolic hydroxyl group onto L-tyrosine was developed. By using this approach, protected L-3-hydroxy-4-methoxy-5-methyl-phenylalanine and L-3-hydroxy-4-methoxy-5-methyl-phenylalanol, which are utilized in efficient syntheses of the relevant tetrahydroisoquinoline alkaloids, were prepared conveniently with high yield (c) 2010 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.024

文献信息

• A new approach to the synthesis of l-3-hydroxy-4-methoxy-5-methyl-phenylalanine derivatives from l-tyrosine
  作者：Ruijiao Chen、Deguang Zhu、Zuoqiang Hu、Zhiming Zheng、Xiaochuan Chen

  DOI：10.1016/j.tetasy.2009.12.024

  日期：2010.1

  A practical procedure to regioselectively install a methyl group and a phenolic hydroxyl group onto L-tyrosine was developed. By using this approach, protected L-3-hydroxy-4-methoxy-5-methyl-phenylalanine and L-3-hydroxy-4-methoxy-5-methyl-phenylalanol, which are utilized in efficient syntheses of the relevant tetrahydroisoquinoline alkaloids, were prepared conveniently with high yield (c) 2010 Elsevier Ltd All rights reserved.