(S)-1-[(2R,3S)-2-[(2S,3R)-2-(Benzyloxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-butyrylamino]-3-(4-benzyloxy-phenyl)-3-methoxy-propionyl]-piperidine-2-carboxylic acid benzyl ester | 868151-85-3

• 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)-1-[(2R,3S)-2-[(2S,3R)-2-(Benzyloxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-butyrylamino]-3-(4-benzyloxy-phenyl)-3-methoxy-propionyl]-piperidine-2-carboxylic acid benzyl ester
• CAS: 868151-85-3
• 化学式: C₄₉H₆₃N₃O₉Si
• 分子量: 866.139
• InChiKey: ZEPUGGDGLFESTN-DHGBLACQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.61
• 重原子数：
  62.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  132.94
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (S)-1-[(2R,3S)-2-[(2S,3R)-2-(Benzyloxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-butyrylamino]-3-(4-benzyloxy-phenyl)-3-methoxy-propionyl]-piperidine-2-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢氟酸 、 氢气 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 (S)-1-[(2R,3S)-2-((2S,3R)-3-Hydroxy-2-methylamino-butyrylamino)-3-(4-hydroxy-phenyl)-3-methoxy-propionyl]-piperidine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of tripeptide hydrolysate from papuamide A: determination of absolute stereostructure of β-methoxytyrosine

  摘要：

  Four diastereomers, (2R 3R), (2S 3S), (2S,3R) and (2R,3S) at beta-methoxytyrosine (beta-OMeTyr), of the tripeptide hydrolysate, H-(S)-N-MeThr-beta-OMeTyr-(S)-Hpr-OH, from papuamide A have been synthesized. Comparison of the H-1 NMR data of the natural hydrolysate with the four synthetic diastereomers unambiguously establishes the relative and absolute stereochemistry of the methoxytyrosine as 2R,3R. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.023
• 作为产物：
  描述：

  (S)-2-benzyl 1-tert-butyl piperidine-1,2-dicarboxylate 在 盐酸 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 (S)-1-[(2R,3S)-2-[(2S,3R)-2-(Benzyloxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-butyrylamino]-3-(4-benzyloxy-phenyl)-3-methoxy-propionyl]-piperidine-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis of tripeptide hydrolysate from papuamide A: determination of absolute stereostructure of β-methoxytyrosine

  摘要：

  Four diastereomers, (2R 3R), (2S 3S), (2S,3R) and (2R,3S) at beta-methoxytyrosine (beta-OMeTyr), of the tripeptide hydrolysate, H-(S)-N-MeThr-beta-OMeTyr-(S)-Hpr-OH, from papuamide A have been synthesized. Comparison of the H-1 NMR data of the natural hydrolysate with the four synthetic diastereomers unambiguously establishes the relative and absolute stereochemistry of the methoxytyrosine as 2R,3R. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.023