(2R,3S,4R)-2,3-dipivaloxy-4-methylbutyrolactone | 170312-52-4

• 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: (2R,3S,4R)-2,3-dipivaloxy-4-methylbutyrolactone
• 英文别名: [(2R,3S,4R)-4-(2,2-dimethylpropanoyloxy)-2-methyl-5-oxooxolan-3-yl] 2,2-dimethylpropanoate
• CAS: 170312-52-4
• 化学式: C₁₅H₂₄O₆
• 分子量: 300.352
• InChiKey: QDSFMATUTKHIIC-KXUCPTDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-2,3-dipivaloxy-4-methylbutyrolactone 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以90%的产率得到(2R,3R,4R)-2,3-dihydroxy-4-methylbutyrolactone
  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
• 作为产物：
  描述：

  (2R,3R)-methyl 4-chloro-4-oxo-2,3-dipivaloxybutanoate 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 8.25h， 生成 (2R,3S,4R)-2,3-dipivaloxy-4-methylbutyrolactone
  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

• Optically Pure Dihydroxy γ-Alkylated γ-Butyrolactones Starting from <scp>l</scp>-Tartaric Acid:  Application to Formal and Total Syntheses of Natural Products
  作者：Anne-Marie Fernandez、Jean-Christophe Plaquevent、Lucette Duhamel

  DOI：10.1021/jo970117e

  日期：1997.6.13

  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.