(2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-succinic acid 1-methyl ester | 181589-96-8

• 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,3S)-2-tert-Butoxycarbonylamino-3-methyl-succinic acid 1-methyl ester
• 英文别名: (2S,3S)-3-[(N-Boc)amino]-4-methoxy-2-methyl-4-oxobutanoic acid
• CAS: 181589-96-8
• 化学式: C₁₁H₁₉NO₆
• 分子量: 261.275
• InChiKey: ASDKLNBHJGUFRY-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.77
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  101.93
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-succinic acid 1-methyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 19.25h， 生成 (+/-)-threo-3-methylaspartic acid
  参考文献：
  名称：

  Synthesis of optically active β-alkyl aspartate via [3,3] sigmatropic rearrangement of α-acyloxytrialkylsilane

  摘要：

  The synthesis of four types of optically active beta-carbon-substituted analogs of threo-beta-hydroxy aspartate (THA) and a beta-carbon- substituted analog of threo-beta-benzyloxy aspartate (TBOA), which are potent blockers of excitatory amino acid transporters in the mammalian central nervous system, via the chirality-transferring ester-enolate Claisen rearrangement of alpha-acyloxytrialkylsilane is described. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.157
• 作为产物：
  描述：

  (2S,3R)-3-methyl-2-(tert-butyloxycarbonylamino)-pent-4-enoic acid methyl ester 在 臭氧 、 二甲基硫 、 chromium(VI) oxide 、 硫酸 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 反应 1.17h， 以47%的产率得到(2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-succinic acid 1-methyl ester
  参考文献：
  名称：

  Synthesis of optically active β-alkyl aspartate via [3,3] sigmatropic rearrangement of α-acyloxytrialkylsilane

  摘要：

  The synthesis of four types of optically active beta-carbon-substituted analogs of threo-beta-hydroxy aspartate (THA) and a beta-carbon- substituted analog of threo-beta-benzyloxy aspartate (TBOA), which are potent blockers of excitatory amino acid transporters in the mammalian central nervous system, via the chirality-transferring ester-enolate Claisen rearrangement of alpha-acyloxytrialkylsilane is described. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.157

文献信息

• Purified <i>m</i> CPBA, a Useful Reagent for the Oxidation of Aldehydes
  作者：Alexander Horn、Uli Kazmaier

  DOI：10.1002/ejoc.201701645

  日期：2018.6.7

  Purified mCPBA is a useful reagent for the oxidation of several classes of aldehyde. Although linear unbranched aliphatic aldehydes are oxidized to the corresponding carboxylic acids, α‐branched ones undergo Baeyer–Villiger oxidation to formates. α‐Branched α,β‐unsaturated aldehydes provide enolformates and/or epoxides, which can be saponified to α‐hydroxy ketones with shortening of the carbon chain by

  纯化米CPBA为几类醛的氧化的有用试剂。尽管线性直链脂肪醛被氧化为相应的羧酸，但α支链的醛经过BAeyer-Villiger氧化形成甲酸酯。α-支化的α，β-不饱和醛提供烯醇式和/或环氧化物，可将其皂化为α-羟基酮，且碳链缩短1个碳。未支化的α，β-不饱和醛会经历有趣的BAeyer-Villiger氧化/环氧化/甲酸酯迁移/ BV氧化级联反应，这会导致甲酰保护的水合物整体损失两个碳原子。
• [EN] 1,2,4-OXADIAZOLE DERIVATIVES AS DIPEPTIDYL PEPTIDASE-IV INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES<br/>[FR] DERIVES DE 1,2,4-OXADIAZOLE EN TANT QU'INHIBITEURS DE LA DIPEPTIDYLPEPTIDASE-IV DANS LE TRAITEMENT OU LA PREVENTION DE DIABETES
  申请人：MERCK & CO INC

  公开号：WO2005108382A1

  公开（公告）日：2005-11-17

  The present invention is directed to novel 1,2,4-oxadiazole derivatives which are inhibitors of the dipeptidyl peptidase-IV enzyme ('DP-IV inhibitors') and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及一种新颖的1,2,4-噁二唑衍生物，这些衍生物是二肽基肽酶-IV酶（'DP-IV抑制剂'）的抑制剂，并且在治疗或预防涉及二肽基肽酶-IV酶的疾病方面具有用处，例如糖尿病，特别是2型糖尿病。该发明还涉及包含这些化合物的药物组合物，以及这些化合物和组合物在预防或治疗涉及二肽基肽酶-IV酶的疾病方面的用途。