2,3-O-isopropylidene-γ-D-ribonolactone 2-butylacetoacetate | 259800-88-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2,3-O-isopropylidene-γ-D-ribonolactone 2-butylacetoacetate
• 英文别名: [(3aR,6R,6aR)-2,2-dimethyl-4-oxo-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-6-yl]methyl 2-acetylhexanoate
• CAS: 259800-88-9
• 化学式: C₁₆H₂₄O₇
• 分子量: 328.362
• InChiKey: HFIWFUQEYLDMRJ-KIGPFUIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3-O-isopropylidene-γ-D-ribonolactone 2-butylacetoacetate 在 sodium hydride 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 36.25h， 生成 (4R)-4-butyl-3-methyl-4-(2-naphthylmethyl)-2-pyrazolin-5-one
  参考文献：
  名称：

  Asymmetric synthesis of quaternary α-amino acids using d-ribonolactone acetonide as chiral auxiliary

  摘要：

  We describe a new simple methodology to prepare enantiopure alpha,alpha-dialkylglycines based on the use of commercially available D-ribonolactone as a chiral auxiliary. Enantiopure alpha-methyl and alpha-butyl series are prepared through diastereoselective alkylation and subsequent Schmidt rearrangement of alpha,alpha-dialkylacetoacetates of D-ribonolactone acetonide. Absolute configuration was assigned through preparation of enantiopure 4,4-disubstituted 3-methyl-2-pyrazolin-5-ones. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00457-7
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 在 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 48.25h， 生成 2,3-O-isopropylidene-γ-D-ribonolactone 2-butylacetoacetate
  参考文献：
  名称：

  Asymmetric synthesis of quaternary α-amino acids using d-ribonolactone acetonide as chiral auxiliary

  摘要：

  We describe a new simple methodology to prepare enantiopure alpha,alpha-dialkylglycines based on the use of commercially available D-ribonolactone as a chiral auxiliary. Enantiopure alpha-methyl and alpha-butyl series are prepared through diastereoselective alkylation and subsequent Schmidt rearrangement of alpha,alpha-dialkylacetoacetates of D-ribonolactone acetonide. Absolute configuration was assigned through preparation of enantiopure 4,4-disubstituted 3-methyl-2-pyrazolin-5-ones. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00457-7

文献信息

• Asymmetric synthesis of quaternary α-amino acids using d-ribonolactone acetonide as chiral auxiliary
  作者：Marcial Moreno-Mañas、Elisenda Trepat、Rosa M. Sebastián、Adelina Vallribera

  DOI：10.1016/s0957-4166(99)00457-7

  日期：1999.10

  We describe a new simple methodology to prepare enantiopure alpha,alpha-dialkylglycines based on the use of commercially available D-ribonolactone as a chiral auxiliary. Enantiopure alpha-methyl and alpha-butyl series are prepared through diastereoselective alkylation and subsequent Schmidt rearrangement of alpha,alpha-dialkylacetoacetates of D-ribonolactone acetonide. Absolute configuration was assigned through preparation of enantiopure 4,4-disubstituted 3-methyl-2-pyrazolin-5-ones. (C) 1999 Elsevier Science Ltd. All rights reserved.