(2S)-2-benzamido-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid | 214473-41-3

• 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: (2S)-2-benzamido-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid
• CAS: 214473-41-3
• 化学式: C₁₅H₁₉NO₅
• 分子量: 293.32
• InChiKey: WLKBEJDJCODMSI-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-benzamido-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid 在 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (S)-3-Benzoylamino-N-[(S)-2-(4-hydroxy-3-nitro-phenyl)-1-methoxycarbonyl-ethyl]-succinamic acid
  参考文献：
  名称：

  Convergent synthesis of a fluorescence-quenched glycopeptide as a potential substrate for peptide: N-glycosidases

  摘要：

  The fluorescence-quenched glycopeptide N-gamma-[2-acetamido-6-(2'-amino)benzamido-2,6-dideoxy-beta-D-glucopyranosyl]-N-alpha-benzoyl-Asn-Tyr(NO2)-OMe, having anthranilamide/3-nitrotyrosine as the donor/acceptor pair, was synthesized via a convergent route involving the EEDQ-mediated coupling of 2-acetamido-2,3-di-O-acetyl-6-(2'-tert-butoxycarbonylamino)benzamido-2,6-dideoxy-beta-D-glucopyranosylamine with N-benzoyl-Asp-Tyr(NO2)-OMe, followed by deprotection. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00011-1
• 作为产物：
  描述：

  L-天门冬氨酸-4-叔丁基酯 、 苯甲酰氯 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.33h， 以94%的产率得到(2S)-2-benzamido-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid
  参考文献：
  名称：

  Convergent synthesis of a fluorescence-quenched glycopeptide as a potential substrate for peptide: N-glycosidases

  摘要：

  The fluorescence-quenched glycopeptide N-gamma-[2-acetamido-6-(2'-amino)benzamido-2,6-dideoxy-beta-D-glucopyranosyl]-N-alpha-benzoyl-Asn-Tyr(NO2)-OMe, having anthranilamide/3-nitrotyrosine as the donor/acceptor pair, was synthesized via a convergent route involving the EEDQ-mediated coupling of 2-acetamido-2,3-di-O-acetyl-6-(2'-tert-butoxycarbonylamino)benzamido-2,6-dideoxy-beta-D-glucopyranosylamine with N-benzoyl-Asp-Tyr(NO2)-OMe, followed by deprotection. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00011-1

文献信息

• A Reinvestigation of the α-Alkylation of 4-Monosubstituted 2-phenyloxazol-5(4<i>H</i>)-ones (‘azlactones’): A general entry into highly functionalized α,α-disubstituted α-amino acids
  作者：Daniel Obrecht、Udo Bohdal、Ruth Ruffieux、Klaus Müller

  DOI：10.1002/hlca.19940770520

  日期：1994.8.10

  Novel, more reliable and general reaction conditions for the α-alkylation of 4-monosubstituted 2-phenyloxazol-5(4H)-ones ( = 4-monosubstituted 2-phenyl-azlactones) rac-2 to 4,4-disubstituted 2-phenyloxazol-5(4H)-ones rac-1 were found (Scheme 2). Thus, a whole range of highly functionalized rac-1 were prepared in medium-to-good overall yields (40-90%, see Table). Azlactones rac-1 are ideal precursors

  4-单取代的2-苯基恶唑-5（4 H）-ones（= 4-单取代的2-苯基-氮杂内酯）rac - 2至4,4-二取代的2-的α-烷基化的新颖，更可靠，更通用的反应条件发现苯恶唑-5（4 H）-one rac - 1（方案2）。因此，以中等到良好的总收率（40-90％，见表）制备了一系列高度功能化的rac - 1。lac内酯rac - 1是合成光学纯α，α-二取代（R）和（S）的理想前体。）-α-氨基酸。
• Convergent synthesis of a fluorescence-quenched glycopeptide as a potential substrate for peptide: N-glycosidases
  作者：Vito Ferro、Larry Weiler、Stephen G. Withers

  DOI：10.1016/s0008-6215(98)00011-1

  日期：1998.1

  The fluorescence-quenched glycopeptide N-gamma-[2-acetamido-6-(2'-amino)benzamido-2,6-dideoxy-beta-D-glucopyranosyl]-N-alpha-benzoyl-Asn-Tyr(NO2)-OMe, having anthranilamide/3-nitrotyrosine as the donor/acceptor pair, was synthesized via a convergent route involving the EEDQ-mediated coupling of 2-acetamido-2,3-di-O-acetyl-6-(2'-tert-butoxycarbonylamino)benzamido-2,6-dideoxy-beta-D-glucopyranosylamine with N-benzoyl-Asp-Tyr(NO2)-OMe, followed by deprotection. (C) 1998 Elsevier Science Ltd. All rights reserved.