(2R,3S,4R)-2,3-dihydroxy-4-butylbutyrolactone | 133710-18-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R)-2,3-dihydroxy-4-butylbutyrolactone
• 英文别名: (2R,3R,4R)-2,3-dihydroxy-4-n-butylbutyrolactone；(3R,4R,5R)-5-butyl-3,4-dihydroxyoxolan-2-one
• CAS: 133710-18-6
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: GKGLPUYKMWWENI-DSYKOEDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-2,3-dihydroxy-4-butylbutyrolactone 在 咪唑 、 tri-iodoimidazole 、 三苯基膦 、 锌 作用下， 以 甲苯 为溶剂， 以59%的产率得到(R)-oct-2-en-4-olide
  参考文献：
  名称：

  Yoda, Hidemi; Shirakawa, Koji; Takabe, Kunihiko, Chemistry Letters, 1991, # 3, p. 489 - 490

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,3S,4R)-methyl-2,3-dipivaloxy-4-hydroxyoctanoate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以88%的产率得到(2R,3S,4R)-2,3-dihydroxy-4-butylbutyrolactone
  参考文献：
  名称：

  Optically Pure Dihydroxy γ-Alkylated γ-Butyrolactones Starting from l-Tartaric Acid:  Application to Formal and Total Syntheses of Natural Products

  摘要：

  A general and efficient preparation of epimeric optically pure gamma-butyrolactones 2 and 3 is described starting from L-tartaric acid (1). These lactones are well-known to be important building blocks in the syntheses of natural products. L-Tartaric acid (1) was transformed into carbonylated chirons (ketones 4 and aldehyde 5). These chirons, when submitted to highly stereoselective reactions (reduction or organometallic addition), led to epimeric dihydroxy gamma-butyrolactones 2 and 3 after lactonization and deprotection steps. The resulting optically pure lactones are precursors of biological compounds and have allowed a total synthesis of L-biopterin and formal syntheses of quercus lactone, dodecanolactone, avenaciolide, and tetrahydrocerulenin.

  DOI：

  10.1021/jo970117e

文献信息

• Stereoselective syntheses of γ-alkyl (aryl)-α,β-dihydroxy-γ-butyrolactones and naturally occurring lipid guggultetrol
  作者：Kavirayani R. Prasad、Appayee Chandrakumar

  DOI：10.1016/j.tet.2006.12.037

  日期：2007.2

  gamma-Oxo-butyramides derived from tartaric acid serve as excellent precursors for the synthesis of gamma-alkyl (aryl)-alpha,beta-dihydroxy-gamma-butyrolactones and for the synthesis of tetrols containing three contiguous stereogenic centres. The methodology presented here is general for the synthesis of gamma-alkyl (aryl)-alpha,beta-dihydroxy-gamma-butyrolactones. Utility of the chiral building block was demonstrated by the synthesis of naturally occurring lipid guggultetrol. (c) 2006 Elsevier Ltd. All rights reserved.