(+)-Methyl β,γ-dihydroxy-α-methylenebutyrate | 73945-71-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (+)-Methyl β,γ-dihydroxy-α-methylenebutyrate
• 英文别名: methyl (S)-3,4-dihydroxy-2-methylenebutanoate；methyl (3S)-3,4-dihydroxy-2-methylidenebutanoate
• CAS: 73945-71-8
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: OAVZGKBBHXFFGL-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (+)-Methyl β,γ-dihydroxy-α-methylenebutyrate 在 lithium hydroxide monohydrate 、 camphor-10-sulfonic acid 作用下， 以 水 、 乙腈 为溶剂， 生成 (+)-(S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)acrylic acid
  参考文献：
  名称：

  A New Template of MIitsunobu Acylate Cleavable in Non-Alkaline Conditions

  摘要：

  DOI：

  10.3987/com-21-14562
• 作为产物：
  描述：

  (S)-2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-propenal 在 sodium hydride 、 溶剂黄146 、 silver(l) oxide 作用下， 以 六甲基磷酰三胺 、 水 为溶剂， 反应 43.25h， 生成 (+)-Methyl β,γ-dihydroxy-α-methylenebutyrate
  参考文献：
  名称：

  Synthesis of (S)-(+)-methyl .BETA.,.GAMMA.-dihydroxy-.ALPHA.-methylenebutyrate and (S)-(-)-tulipalin B.

  摘要：

  已成功合成(S)-(+)-甲基β, γ-二羟基-α-亚甲基丁酸酯和(S)-(-)-郁金香醇B，这些是从Thunberg的海枣(SPIRAEA thunbergii Sieb.)中分离的抗菌物质，起始原料为异丙基羟基-D-甘油醛。

  DOI：

  10.1271/bbb1961.44.199

文献信息

• 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.
• Synthesis of (S)-(+)-methyl .BETA.,.GAMMA.-dihydroxy-.ALPHA.-methylenebutyrate and (S)-(-)-tulipalin B.
  作者：Akira TANAKA、Kyohei YAMASHITA

  DOI：10.1271/bbb1961.44.199

  日期：——

  The synthesis of (S)-(+)-methyl β, γ-dihydroxy-α-methylenebutyrate and (S)-(-)-tulipalin B, antibacterial substances isolated from Spiraea thunliergii Sieb. has been accomplished starting from isopropylidene-D-glyceraldehyde.

  已成功合成(S)-(+)-甲基β, γ-二羟基-α-亚甲基丁酸酯和(S)-(-)-郁金香醇B，这些是从Thunberg的海枣(SPIRAEA thunbergii Sieb.)中分离的抗菌物质，起始原料为异丙基羟基-D-甘油醛。
• A New Template of MIitsunobu Acylate Cleavable in Non-Alkaline Conditions
  作者：Kengo Shigetomi、Yoshimichi Sakakibara、Yusuke Sai、Yasumitsu Uraki、Makoto Ubukata

  DOI：10.3987/com-21-14562

  日期：——