(2R,3R,4R)-2,3-dihydroxy-4-methylbutyrolactone | 140632-62-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2R,3R,4R)-2,3-dihydroxy-4-methylbutyrolactone
• 英文别名: (2R,3S,4S)-2,3-dihydroxy-4-methylbutyrolactone；(3R,4R,5R)-3,4-dihydroxy-5-methyloxolan-2-one
• CAS: 140632-62-8
• 化学式: C₅H₈O₄
• 分子量: 132.116
• InChiKey: JYHWQRJRDKSSIF-FLRLBIABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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,3R,4R)-2,3-dihydroxy-4-methylbutyrolactone 在 2,6-二甲基吡啶 、 戴斯-马丁氧化剂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.33h， 生成 ethyl (4R,5R)-4,5-bis(tert-butyldimethylsilyloxy)-2-diazo-3,6-dioxoheptanoate
  参考文献：
  名称：

  Selectivity in the cycloadditions of carbonyl ylides with glyoxylates: an approach to the zaragozic acids—squalestatins

  摘要：

  在催化量的醋酸铑(II)存在下，二氮二酮酯8与甘油二酸酯反应，以良好产率生成6,8-二氧双环[3.2.1]辛烷9和11。对9的进一步修饰提供了适合的醇25，通过酸催化重排可得到2,8-二氧双环[3.2.1]辛烷骨架26，这是扎戈西酸——角鲨烷抑制剂的结构部分。更多取代的二氮二酮酯36和40也能与甘油二酸酯发生高度区域选择性和立体选择性的环加成反应，生成环加成产物41、43和44。

  DOI：

  10.1039/b004870o
• 作为产物：
  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

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.
• Selectivity in the cycloadditions of carbonyl ylides with glyoxylates: an approach to the zaragozic acids—squalestatins
  作者：David M. Hodgson、James M. Bailey、Carolina Villalonga-Barber、Michael G. B. Drew、Timothy Harrison

  DOI：10.1039/b004870o

  日期：——

  Reaction of diazodiketoester 8 with glyoxylates in the presence of catalytic rhodium(II) acetate generates 6,8-dioxabicyclo[3.2.1]octanes 9 and 11 in good yield. Elaboration of 9 provides a suitable alcohol 25 for acid-catalysed rearrangement to give the 2,8-dioxabicyclo[3.2.1]octane skeleton 26 of the zaragozic acids—squalestatins. More substituted diazodiketoesters 36 and 40 also undergo highly regio- and diastereoselective cycloaddition with glyoxylates to give the cycloadducts 41, 43 and 44.

  在催化量的醋酸铑(II)存在下，二氮二酮酯8与甘油二酸酯反应，以良好产率生成6,8-二氧双环[3.2.1]辛烷9和11。对9的进一步修饰提供了适合的醇25，通过酸催化重排可得到2,8-二氧双环[3.2.1]辛烷骨架26，这是扎戈西酸——角鲨烷抑制剂的结构部分。更多取代的二氮二酮酯36和40也能与甘油二酸酯发生高度区域选择性和立体选择性的环加成反应，生成环加成产物41、43和44。
• 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.