(2S,3R)-2-[(4,4-Dimethyl-2,6-dioxo-cyclohexylidenemethyl)-amino]-3-hydroxy-butyric acid | 849829-35-2

• 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,3R)-2-[(4,4-Dimethyl-2,6-dioxo-cyclohexylidenemethyl)-amino]-3-hydroxy-butyric acid
• 英文别名: (2S,3R)-2-[(4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino]-3-hydroxybutanoic acid
• CAS: 849829-35-2
• 化学式: C₁₃H₁₉NO₅
• 分子量: 269.298
• InChiKey: ZNIAPLLWBWWEJP-HQJQHLMTSA-N

物化性质

• 沸点：
  476.5±45.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.25
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  103.7
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-[(4,4-Dimethyl-2,6-dioxo-cyclohexylidenemethyl)-amino]-3-hydroxy-butyric acid 在 palladium on activated charcoal 四乙基溴化铵 、 氢气 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 tert-butyl (2S,3R)-2-[(4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino]-3-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxybutanoate
  参考文献：
  名称：

  Nα-Dmc protected amino acid aglycones: versatile hydrogenolysis stable acceptors for O-glycosylation

  摘要：

  N-alpha-(4,4-Dimethyl-2,6-dioxocyclohexylidenemethylene) (Dmc) protected l-serine, L-threonine and L-homoserine have been prepared as tert-butyl esters in excellent yields. These hydrogenolysis stable acceptors underwent efficient alpha-O-glycosylation with an L-fucopyranosyl bromide donor and also allowed convenient protecting group manipulations to ultimately deliver novel glycoamino acid building blocks suitable for Fmoc based solid-phase glycopeptide synthesis. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.055
• 作为产物：
  描述：

  L-苏氨酸 、 2-dimethylaminomethylene-5,5-dimethylcyclohexane-1,3-dione 以 乙醇 为溶剂， 以86%的产率得到(2S,3R)-2-[(4,4-Dimethyl-2,6-dioxo-cyclohexylidenemethyl)-amino]-3-hydroxy-butyric acid
  参考文献：
  名称：

  Nα-Dmc protected amino acid aglycones: versatile hydrogenolysis stable acceptors for O-glycosylation

  摘要：

  N-alpha-(4,4-Dimethyl-2,6-dioxocyclohexylidenemethylene) (Dmc) protected l-serine, L-threonine and L-homoserine have been prepared as tert-butyl esters in excellent yields. These hydrogenolysis stable acceptors underwent efficient alpha-O-glycosylation with an L-fucopyranosyl bromide donor and also allowed convenient protecting group manipulations to ultimately deliver novel glycoamino acid building blocks suitable for Fmoc based solid-phase glycopeptide synthesis. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.055

文献信息

• Nα-Dmc protected amino acid aglycones: versatile hydrogenolysis stable acceptors for O-glycosylation
  作者：Barrie Kellam、Paul A. Ward、Aisyah S. Abdul Rahim、Siri Ram Chhabra

  DOI：10.1016/j.tetlet.2005.01.055

  日期：2005.3

  N-alpha-(4,4-Dimethyl-2,6-dioxocyclohexylidenemethylene) (Dmc) protected l-serine, L-threonine and L-homoserine have been prepared as tert-butyl esters in excellent yields. These hydrogenolysis stable acceptors underwent efficient alpha-O-glycosylation with an L-fucopyranosyl bromide donor and also allowed convenient protecting group manipulations to ultimately deliver novel glycoamino acid building blocks suitable for Fmoc based solid-phase glycopeptide synthesis. (C) 2005 Elsevier Ltd. All rights reserved.