3,5-二溴酪氨酸甲酯盐酸盐 | 61039-29-0

• 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
• 中文名称: 3,5-二溴酪氨酸甲酯盐酸盐
• 英文名称: 3,5-dibromotyrosine methyl ester hydrochloride
• 英文别名: 3,5-dibromo-L-tyrosine methyl ester; hydrochloride；3,5-Dibrom-L-tyrosin-methylester; Hydrochlorid；(S)-Methyl 2-amino-3-(3,5-dibromo-4-hydroxyphenyl)propanoate hydrochloride；methyl (2S)-2-amino-3-(3,5-dibromo-4-hydroxyphenyl)propanoate;hydrochloride
• CAS: 61039-29-0
• 化学式: C₁₀H₁₁Br₂NO₃*ClH
• 分子量: 389.471
• InChiKey: WBWBPCPGLKUMGJ-QRPNPIFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.75
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-二溴酪氨酸甲酯盐酸盐 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 sodium acetate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 三氟乙酸 、 thallium(III) nitrate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (9S,12S,15S)-9-tert-Butoxycarbonylamino-4-hydroxy-12-((R)-1-hydroxy-ethyl)-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3,5,7(22),17(21),18-hexaene-15-carboxylic acid
  参考文献：
  名称：

  Synthesis and structural revision of eurypamides isolated from the Palauan sponge Microciona eurypa

  摘要：

  Eurypamides A and B, 1 and 2, were successfully synthesized by employing Tl(NO3)(3) (TTN) oxidation of the corresponding halogenated phenols, 9, 16, and 26. This investigation revealed that the dihydroxyarginine residue of 1 should be revised to possess (2S,3R,4S)-configuration. In addition, the synthesis of 2 provided a pure sample, which was previously characterized in a mixture. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.105
• 作为产物：
  描述：

  N-formyl-L-tyrosine methyl ester 在 盐酸 、 溴 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 3,5-二溴酪氨酸甲酯盐酸盐
  参考文献：
  名称：

  新型抗真菌抗生素哌嗪霉素的合成

  摘要：

  Piperazinomycin是一种新型抗真菌抗生素，是从四溴酪氨酰酪氨酸合成的，其与三硝酸th（TTN）的氧化可导致形成一个类似于Piperazinomycin的应变14元环，这是关键步骤。

  DOI：

  10.1016/s0040-4039(00)84984-9

文献信息

• Total synthesis of eurypamides, marine cyclic-isodityrosines from the Palauan sponge Microciona eurypa
  作者：Miyuki Ito、Maki Yamanaka、Noriki Kutsumura、Shigeru Nishiyama

  DOI：10.1016/j.tet.2004.04.062

  日期：2004.6

  Total synthesis of eurypamides A, B, and D, 1, 2, and 4, has been successfully accomplished. The Tl(NO3)(3) (TTN) oxidation of the halogenated bisphenols, 14a, 14b, 24, and 43, effected regio-controlled cyclization to provide the corresponding diaryl ethers, 15a, 15b, 25, and 46. This investigation revealed a structural revision of eurypamide A as to possess (2"S,3"R,4"S)-configuration (47), along with the spectral data of pure 2 and 4, which were previously characterized in a mixture. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of piperazinomycin, a novel antifungal antibiotic
  作者：Shigeru Nishiyama、Kazuhiko Nakamura、Yoshikazu Suzuki、Shosuke Yamamura

  DOI：10.1016/s0040-4039(00)84984-9

  日期：——

  Piperazinomycin, a novel antifugal antibiotic, has been synthesized from tetrabromotyrosyltyrosine, whose oxidation with thallium trinitrate (TTN) leads to the formation of a strained 14-membered ring similar to that of piperazinomycin as a key step.

  Piperazinomycin是一种新型抗真菌抗生素，是从四溴酪氨酰酪氨酸合成的，其与三硝酸th（TTN）的氧化可导致形成一个类似于Piperazinomycin的应变14元环，这是关键步骤。
• Synthesis and structural revision of eurypamides isolated from the Palauan sponge Microciona eurypa
  作者：Miyuki Ito、Maki Yamanaka、Noriki Kutsumura、Shigeru Nishiyama

  DOI：10.1016/j.tetlet.2003.08.105

  日期：2003.10

  Eurypamides A and B, 1 and 2, were successfully synthesized by employing Tl(NO3)(3) (TTN) oxidation of the corresponding halogenated phenols, 9, 16, and 26. This investigation revealed that the dihydroxyarginine residue of 1 should be revised to possess (2S,3R,4S)-configuration. In addition, the synthesis of 2 provided a pure sample, which was previously characterized in a mixture. (C) 2003 Elsevier Ltd. All rights reserved.