Boc-HyAsn(OTBS)-OH | 159351-28-7

• 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: Boc-HyAsn(OTBS)-OH
• 英文别名: (2S,3R)-4-amino-3-[tert-butyl(dimethyl)silyl]oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoic acid
• CAS: 159351-28-7
• 化学式: C₁₅H₃₀N₂O₆Si
• 分子量: 362.499
• InChiKey: MKDDRGBWQRYKES-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-HyAsn(OTBS)-OH 、 L-苯丙氨酸甲酯盐酸盐 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以68%的产率得到methyl ((2S,3R)-4-amino-2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)-4-oxobutanoyl)-L-phenylalaninate
  参考文献：
  名称：

  Asymmetric synthesis of erythro-β-hydroxyasparagine

  摘要：

  erythro-Hydroxyasparagine (eHyAsn, 1) occurs ill a number of naturally occurring peptides and proteins. Previous syntheses have relied on enzyme-catalyzed reactions to produce relevant, optically active intermediates. We report herein a completely chemical synthesis that intercepts Boger's synthesis of the diastereomer (tHyAsn, 4), utilizing a Sharpless asymmetric aminohydroxylation reaction to introduce the two stereocenters. Boc-HyAsn(OTBS)-OH (10) was Coupled effectively with phenylalanine methyl ester using EDC/HOBt. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.103
• 作为产物：
  描述：

  在 ruthenium trichloride 、 sodium periodate 、 碳酸氢钠 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 以73%的产率得到Boc-HyAsn(OTBS)-OH
  参考文献：
  名称：

  Asymmetric synthesis of erythro-β-hydroxyasparagine

  摘要：

  erythro-Hydroxyasparagine (eHyAsn, 1) occurs ill a number of naturally occurring peptides and proteins. Previous syntheses have relied on enzyme-catalyzed reactions to produce relevant, optically active intermediates. We report herein a completely chemical synthesis that intercepts Boger's synthesis of the diastereomer (tHyAsn, 4), utilizing a Sharpless asymmetric aminohydroxylation reaction to introduce the two stereocenters. Boc-HyAsn(OTBS)-OH (10) was Coupled effectively with phenylalanine methyl ester using EDC/HOBt. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.103

文献信息

• Asymmetric synthesis of erythro-β-hydroxyasparagine
  作者：Douglas Wong、Carol M. Taylor

  DOI：10.1016/j.tetlet.2008.12.103

  日期：2009.3

  erythro-Hydroxyasparagine (eHyAsn, 1) occurs ill a number of naturally occurring peptides and proteins. Previous syntheses have relied on enzyme-catalyzed reactions to produce relevant, optically active intermediates. We report herein a completely chemical synthesis that intercepts Boger's synthesis of the diastereomer (tHyAsn, 4), utilizing a Sharpless asymmetric aminohydroxylation reaction to introduce the two stereocenters. Boc-HyAsn(OTBS)-OH (10) was Coupled effectively with phenylalanine methyl ester using EDC/HOBt. (C) 2009 Elsevier Ltd. All rights reserved.