(S)-methyl N-(tert-butyloxycarbonyl)-β³-homo-3,4-bis(benzyloxy)phenylalanine carboxylate | 503416-72-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-methyl N-(tert-butyloxycarbonyl)-β³-homo-3,4-bis(benzyloxy)phenylalanine carboxylate
• 英文别名: Boc-β³-(L)-DOPA[OBn]2-OMe；methyl (3S)-4-[3,4-bis(phenylmethoxy)phenyl]-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 503416-72-6
• 化学式: C₃₀H₃₅NO₆
• 分子量: 505.611
• InChiKey: KZMZMRGKDHUOSY-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  3.0
• 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：

  (S)-methyl N-(tert-butyloxycarbonyl)-β³-homo-3,4-bis(benzyloxy)phenylalanine carboxylate 在 palladium on activated charcoal 氢气 、 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~60.0 ℃ 、344.5 kPa 条件下， 反应 18.0h， 生成 Boc-[18-C-6]-β³-(L)-DOPA-OMe
  参考文献：
  名称：

  Synthesis of [18-C-6]-β3-(L)-DOPA, first β-amino acid with a crown-ether receptor side-chain

  摘要：

  Terminally protected Boc-beta(3)-(L)-DOPA-OMe has been synthesized from (L)-DOPA by the Arndt-Eistert homologation procedure. Then, a first crown-ether derivative, Boc-[18-C-6]-beta(3)-(L)-DOPA-OMe. has been obtained by bis-O-alkylation of the catechol function with cyclization, using Cs2CO3 as base and pentaethyleneglycol ditosylate as alkylating agent, in DMF at 60degreesC. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02035-x
• 作为产物：
  描述：

  N-BOC-3-羟基-L-酪氨酸甲酯 在 sodium hydroxide 、 silver benzoate 、 氯甲酸乙酯 、 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 18.25h， 生成 (S)-methyl N-(tert-butyloxycarbonyl)-β³-homo-3,4-bis(benzyloxy)phenylalanine carboxylate
  参考文献：
  名称：

  Synthesis of [18-C-6]-β3-(L)-DOPA, first β-amino acid with a crown-ether receptor side-chain

  摘要：

  Terminally protected Boc-beta(3)-(L)-DOPA-OMe has been synthesized from (L)-DOPA by the Arndt-Eistert homologation procedure. Then, a first crown-ether derivative, Boc-[18-C-6]-beta(3)-(L)-DOPA-OMe. has been obtained by bis-O-alkylation of the catechol function with cyclization, using Cs2CO3 as base and pentaethyleneglycol ditosylate as alkylating agent, in DMF at 60degreesC. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02035-x

文献信息

• Synthesis of terminally protected (S)-β3-H-DOPA by Arndt–Eistert homologation: an approach to crowned β-peptides
  作者：Anne Gaucher、Laurence Dutot、Olivier Barbeau、Wahib Hamchaoui、Michel Wakselman、Jean-Paul Mazaleyrat

  DOI：10.1016/j.tetasy.2004.11.089

  日期：2005.2

  Terminally protected Boc-(,S)-beta(3)-H-DOPA-OMe has been synthesized from L-DOPA by the Arndt-Eistert homologation procedure. During the synthesis, the side-chain catechol group was temporarily protected by benzylation. The absence of racemization was demonstrated by F-19 NMR analysis of the (+)-(R)- and (-)-(S)-alpha-methoxy-alpha-trifluoromethyl-alpha-phenyl-acetamide derivatives. The catechol function of Boc-(S)-beta(3)-H-DOPA-OMe may be used for crown-ether formation, a step towards the construction of crowned beta-peptides. (C) 2004 Elsevier Ltd. All rights reserved.