(2R,3S,4R)-methyl-2,3-dipivaloxy-4-hydroxypentanoate | 170312-48-8

• 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)-methyl-2,3-dipivaloxy-4-hydroxypentanoate
• 英文别名: methyl (2R,3S,4R)-2,3-bis(2,2-dimethylpropanoyloxy)-4-hydroxypentanoate
• CAS: 170312-48-8
• 化学式: C₁₆H₂₈O₇
• 分子量: 332.394
• InChiKey: YQCBWJOOGYKVAT-OUAUKWLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-methyl-2,3-dipivaloxy-4-hydroxypentanoate 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以97%的产率得到(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
• 作为产物：
  描述：

  (2R,3R)-methyl 4-chloro-4-oxo-2,3-dipivaloxybutanoate 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 4.25h， 生成 (2R,3S,4R)-methyl-2,3-dipivaloxy-4-hydroxypentanoate
  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.