2,3-O-isopropylidene-γ-D-ribonolactone (2R)-2-methyl-(2-naphthylmethyl)acetoacetate | 259800-75-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-O-isopropylidene-γ-D-ribonolactone (2R)-2-methyl-(2-naphthylmethyl)acetoacetate
• 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 (2R)-2-methyl-2-(naphthalen-2-ylmethyl)-3-oxobutanoate
• CAS: 259800-75-4
• 化学式: C₂₄H₂₆O₇
• 分子量: 426.466
• InChiKey: IDTIGGFPCUPVCI-DBYOASNMSA-N

物化性质

• 沸点：
  583.9±50.0 °C(predicted)
• 密度：
  1.230±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 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 (2R)-2-methyl-(2-naphthylmethyl)acetoacetate 在 盐酸 、 titanium(IV) tetraethanolate 、 sodium azide 、 甲烷磺酸 作用下， 以 乙二醇二甲醚 为溶剂， 反应 53.0h， 生成 (S)-α-(2-naphthylmethyl)alanine hydrochloride
  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 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 、 甲苯 为溶剂， 反应 43.25h， 生成 2,3-O-isopropylidene-γ-D-ribonolactone (2R)-2-methyl-(2-naphthylmethyl)acetoacetate
  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.