(3R,4S)-4-hydroxy-3-methyldihydrofuran-2(3H)-one | 112789-85-2

• 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: (3R,4S)-4-hydroxy-3-methyldihydrofuran-2(3H)-one
• 英文别名: (3R,4S)-4-hydroxy-3-methyloxolan-2-one
• CAS: 112789-85-2
• 化学式: C₅H₈O₃
• 分子量: 116.117
• InChiKey: WMWULFWRZYXSIW-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  8
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S)-4-hydroxy-3-methyldihydrofuran-2(3H)-one 在 silver(l) oxide 作用下， 以 乙醇 为溶剂， 生成 (R)-(S)-2-Oxiranyl-propionic acid ethyl ester
  参考文献：
  名称：

  Préparation de nouveaux synthons chiraux: les β,X-époxyesters; Application à la synthèse de β-hydroxyesters énantiomériquement purs

  摘要：

  DOI：

  10.1016/s0040-4039(00)95419-4
• 作为产物：
  描述：

  (2R,3S)-3-Benzyloxy-4-hydroxy-2-methyl-butyric acid methyl ester 生成 (3R,4S)-4-hydroxy-3-methyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  BERNARDI, ANNA;CARDANI, SILVIA;SCOLASTICO, CARLO;VILLA, ROBERTO, TETRAHEDRON, 46,(1990) N, C. 1987-1998

  摘要：

  DOI：

文献信息

• Copper-Catalyzed Asymmetric Allylic Alkylation of Halocrotonates: Efficient Synthesis of Versatile Chiral Multifunctional Building Blocks
  作者：Tim den Hartog、Beatriz Maciá、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1002/adsc.201000109

  日期：——

  The highly enantioselective synthesis of α‐methyl‐substituted esters is reported in up to 90% yield and up to 99% ee using copper‐TaniaPhos as chiral catalyst. The transformation proved scalable to at least 6.6 mmol (1.7 g scale). The products of this transformation have been further elaborated to multifunctional building blocks with a single (branched esters and acids) or multiple stereogenic centers

  据报道，使用铜-TaniaPhos作为手性催化剂，α-甲基取代酯的高度对映选择性合成产率高达90％，ee高达99％。该转化证明可扩展至至少6.6 mmol（1.7 g规模）。这种转化的产物已被进一步精制为具有单个（支链酯和酸）或多个立体中心（邻位二甲基酯以及羟基或碘取代的内酯）的多功能构件。
• New chiral building blocks by microbial asymmetric reduction: A direct access to functionalized 2R,3R- and 2S,3R-2-methyl-3-hydroxy butyrate synthons
  作者：Didier Buisson、Serge Henrot、Marc Larcheveque、Robert Azerad*

  DOI：10.1016/s0040-4039(00)96688-7

  日期：1987.1

  3R)--hydroxyesters in high optical purity. The corresponding (2R,3R)- isomer was obtained, with other strains, only in mixture with the isomer. These esters are useful precursors for chiral 2-methyl-3-hydroxy-butyrolactone synthons.

  几种真菌菌株对4-O-苄基-2-甲基-3-氧代丁酸酯的还原主要产生高光学纯度的（2S，3R）-羟基酯。仅在与异构体混合的情况下，与其他菌株一起获得了相应的（2R，3R）-异构体。这些酯是用于手性2-甲基-3-羟基-丁内酯合成子的有用的前体。
• The antibacterial properties of 6-tuliposide B. Synthesis of 6-tuliposide B analogues and structure–activity relationship
  作者：Kengo Shigetomi、Kazuaki Shoji、Shinya Mitsuhashi、Makoto Ubukata

  DOI：10.1016/j.phytochem.2009.10.008

  日期：2010.2

  6-Tuliposide B is a secondary metabolite occurring specifically in tulip anthers. Recently, a potent antibacterial activity of 6-tuliposide B has been reported. However, its molecular target has not yet been established, nor its action mechanism. To shed light on such issues, 6-tuliposide B and tulipalin B analogues were synthesized and a structure-activity relationship (SAR) was examined using a broad panel of bacterial strains. As the results of SAR among a total of 25 compounds, only tulipalin B and the compounds having 3',4'-dihydroxy-2'-methylenebutanoate (DHMB) moieties showed any significant antibacterial activity. Moreover, the 3'R analogues of these compounds displayed essentially the same activities as 6-tuliposide B and the structure of the 3'R-DMBA moiety was the same as that of the proposed active moiety of cnicin. These results suggest that 6-tuliposide B has the same action mechanism as proposed for cnicin and bacteria) MurA is one of the major molecular targets of 6-tuliposide B. (C) 2009 Elsevier Ltd. All rights reserved.
• BERNARDI, ANNA;CARDANI, SILVIA;SCOLASTICO, CARLO;VILLA, ROBERTO, TETRAHEDRON, 46,(1990) N, C. 1987-1998
  作者：BERNARDI, ANNA、CARDANI, SILVIA、SCOLASTICO, CARLO、VILLA, ROBERTO

  DOI：——

  日期：——
• SHIBATA, IKUYA;MATSUO, FUMIYUKI;BABA, AKIO;MATSUDA, HARUO, J. ORG. CHEM., 56,(1991) N, C. 475-476
  作者：SHIBATA, IKUYA、MATSUO, FUMIYUKI、BABA, AKIO、MATSUDA, HARUO

  DOI：——

  日期：——