(S)-N-benzyloxycarbonyl-4-hydroxy-3-hydroxymethylphenylalanine | 52186-44-4

• 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: (S)-N-benzyloxycarbonyl-4-hydroxy-3-hydroxymethylphenylalanine
• 英文别名: N-(benzyloxycarbonyl)-3-(hydroxymethyl)-(S)-tyrosine；N-benzyloxycarbonyl-3-hydroxymethyl-L-tyrosine；N-Cbz-3-hydroxymethyl-L-tyrosine；(2S)-3-[4-hydroxy-3-(hydroxymethyl)phenyl]-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 52186-44-4
• 化学式: C₁₈H₁₉NO₆
• 分子量: 345.352
• InChiKey: IWGPPEDFANTXOE-HNNXBMFYSA-N

物化性质

• 熔点：
  132-133 °C(Solv: dichloromethane (75-09-2); isopropyl ether (108-20-3))
• 沸点：
  601.3±55.0 °C(Predicted)
• 密度：
  1.370±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-N-benzyloxycarbonyl-4-hydroxy-3-hydroxymethylphenylalanine 在 溴 、 sodium acetate 、 对甲苯磺酸 作用下， 以 溶剂黄146 为溶剂， 反应 3.5h， 生成 N-(benzyloxycarbonyl)-3-bromo-5-(hydroxymethyl)-(S)-tyrosine methyl ester
  参考文献：
  名称：

  对映体纯竞争性NMIDA拮抗剂SDZ 220-581和SDZ EAB 515的替代合成

  摘要：

  描述了从LZ-酪氨酸开始的对映体纯SDZ 220-881 （1a）和SDZ EAB 515 （1b）的另一种合成方法。

  DOI：

  10.1002/hlca.19980810322
• 作为产物：
  描述：

  N-苄氧羰基-L-酪氨酸 在 三氯化硼 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 4.17h， 生成 (S)-N-benzyloxycarbonyl-4-hydroxy-3-hydroxymethylphenylalanine
  参考文献：
  名称：

  A convenient two step transformation of tyrosine into the antihypertensive amino acid (S)-4-hydroxy-3-hydroxymethylphenylalanine

  摘要：

  Treatment of tyrosine with paraformaldehyde and catalytic amounts of p-toluenesulfonic acid, at reflux in toluene, directly generates benzyl (S)-4-(4H-1,3-benzodioxin-6-ylmethyl)-5-oxo-1,3-oxazolane-3-carboxylate, which on treatment with boron trichloride in dichloromethane, affords (S)-4-hydroxy-3-hydroxymethylphenylalanine. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.02.031

文献信息

• An Alternative Synthesis of the Enantiomerically Pure Competitive NMIDA Antagonists SDZ 220-581 and SDZ EAB 515
  作者：Werner Müller、Markus Bänziger、Peter Kipfer

  DOI：10.1002/hlca.19980810322

  日期：——

  An alternative synthesis of enantiomerically pure SDZ 220–881 (1a) and SDZ EAB 515 (1b) starting from L-Z-tyrosine is described.

  描述了从LZ-酪氨酸开始的对映体纯SDZ 220-881 （1a）和SDZ EAB 515 （1b）的另一种合成方法。
• 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.
• Acid-Catalyzed Synthesis of Methylene-Bridged (<i>S</i>)-Tyrosine−Phenol Dimers
  作者：Sean P. Bew、David L. Hughes、Sunil V. Sharma

  DOI：10.1021/jo0610863

  日期：2006.9.1

  The efficient synthesis of 2,2'-arylmethylene dimers from 3-hydroxymethyl or 3-methoxymethyl-5-halo-(S)-tyrosines and para-substituted phenols under acid-catalyzed reaction conditions using either conventional or microwave-assisted protocols is described.
• A convenient two step transformation of tyrosine into the antihypertensive amino acid (S)-4-hydroxy-3-hydroxymethylphenylalanine
  作者：Pietro Allevi、Riccardo Cribiù、Mario Anastasia

  DOI：10.1016/j.tetasy.2004.02.031

  日期：2004.4

  Treatment of tyrosine with paraformaldehyde and catalytic amounts of p-toluenesulfonic acid, at reflux in toluene, directly generates benzyl (S)-4-(4H-1,3-benzodioxin-6-ylmethyl)-5-oxo-1,3-oxazolane-3-carboxylate, which on treatment with boron trichloride in dichloromethane, affords (S)-4-hydroxy-3-hydroxymethylphenylalanine. (C) 2004 Published by Elsevier Ltd.