6-(1,2,3-trihydroxy-heptyl)-5,6-dihydro-pyran-2-one | 179237-96-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-(1,2,3-trihydroxy-heptyl)-5,6-dihydro-pyran-2-one
• 英文别名: (+)-deacetylboronolide；deacetylboronolide；(2R)-2-[(1S,2R,3S)-1,2,3-trihydroxyheptyl]-2,3-dihydropyran-6-one
• CAS: 179237-96-8
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: VNWNEIVQZJXANY-LUTQBAROSA-N

物化性质

• 熔点：
  101 °C
• 沸点：
  504.4±45.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 6-(1,2,3-trihydroxy-heptyl)-5,6-dihydro-pyran-2-one 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到(+)-boronolide
  参考文献：
  名称：

  （+）-硼烷内酯的立体选择性合成

  摘要：

  描述了由戊醛有效地对映和立体控制的（+）-硼烷内酯的全合成。关键步骤包括Sharpless不对称二羟基化反应，螯合控制的Grignard反应，然后进行Sharpless不对称环氧化反应和闭环复分解反应。

  DOI：

  10.1016/j.tetlet.2005.01.120
• 作为产物：
  描述：

  methyl 3,4:5,6-di-O-isopropylidene-D-gluconate 在 palladium on activated charcoal 、 Lindlar's catalyst 咪唑 、 喹啉 、 盐酸 、 4-二甲氨基吡啶 、 正丁基锂 、 氢气 、 二异丁基氢化铝 、 过碘酸 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -78.0~20.0 ℃ 、3.55 MPa 条件下， 反应 103.0h， 生成 6-(1,2,3-trihydroxy-heptyl)-5,6-dihydro-pyran-2-one
  参考文献：
  名称：

  Stereoselective synthesis of (+)-boronolide and its 8-epimer

  摘要：

  从容易获得的碳水化合物开始，以α-氧化醛的非对映选择性炔丙基化为关键步骤，合成了8-表-(+)-硼内酯19和(+)-硼内酯1。

  DOI：

  10.1039/b406397j

文献信息

• Stereocontrolled Synthesis of (+)-Boronolide
  作者：Barry M. Trost、Vince S. C. Yeh

  DOI：10.1021/ol026665i

  日期：2002.10.1

  Boronolide was synthesized stereoselectively from hydroxyacetylfuran 5 and valeraldehyde 6 using a novel dizinc aldol catalyst. Ring closing metathesis provides the lactone ring. The synthesis requires 12 steps and proceeds in 26% overall yield. [reaction: see text]

  使用新型二锌醛醇缩合催化剂从羟乙酰呋喃5和戊醛6立体选择性地合成硼硼化物。闭环易位提供了内酯环。合成需要12个步骤，总产率为26％。[反应：看文字]
• Enantio- and Diastereocontrolled Total Synthesis of (+)-Boronolide
  作者：Pradeep Kumar、S. Vasudeva Naidu

  DOI：10.1021/jo0603781

  日期：2006.5.1

  An efficient stereoselective total synthesis of (+)-boronolide from valeraldehyde is described. The key steps include a Sharpless asymmetric hydroxylation, a chelation-controlled vinyl Grignard reaction followed by a Sharpless asymmetric epoxidation, hydrolytic kinetic resolution, and a ring-closing metathesis.

  描述了由戊醛有效地立体选择性地全合成（+）-硼烷内酯。关键步骤包括Sharpless不对称羟基化，螯合控制的乙烯基Grignard反应，然后进行Sharpless不对称环氧化，水解动力学拆分和闭环复分解反应。
• Synthesis of (+)-boronolide and (+)-deacetylboronolide using Pd-catalyzed carbonylation and lactonization
  作者：Yuji Kurogome、Yasunao Hattori、Hidefumi Makabe

  DOI：10.1016/j.tetlet.2014.03.070

  日期：2014.4

  (+)-Boronolide and (+)-deacetylboronolide were synthesized using Pd-catalyzed CO insertion and lactonization as the key step. As to the C-13 NMR data of (+)-deacetylboronolide, the assignment at C-6 position should be revised. (C) 2014 Elsevier Ltd. All rights reserved.

  （+）-Boronolide 和（+）-去乙酰基Boronolide 通过钯催化的CO 插入和环状酯化作为关键步骤进行合成。关于（+）-去乙酰基Boronolide 的 C-13 核磁共振数据，C-6 位置的赋值需要进行修正。© 2014 Elsevier Ltd. 保留所有权利。
• Total Synthesis of (+)-Boronolide, (+)-Deacetylboronolide, and (+)-Dideacetylboronolide
  作者：M. Chandrasekhar、Kusum L. Chandra、Vinod K. Singh

  DOI：10.1021/jo0269058

  日期：2003.5.1

  Total synthesis of (+)-boronolide, (+)-deacetylboronolide, and (+)-dideacetylboronolide has been achieved from a single intermediate 26, which was synthesized in 11 steps from a D-mannitol-derived intermediate 8 in an overall yield of 10%. The key steps in the synthesis are inversion of a chiral center by taking an advantage of the inherent mechanism involved in the ring closing to an epoxide via intramolecular S(N)2 reaction and lactonization of a diol using Fetizons reagent. The strategy is amenable to preparation of analogues of (+)-boronolide in sufficient amount for further screening of biological activity.
• Erythrulose derivatives as functionalized chiral d3 and d4 synthons
  作者：Juan Murga、Eva Falomir、Miguel Carda、J.Alberto Marco

  DOI：10.1016/s0957-4166(02)00638-9

  日期：2002.10

  Protected erythrulose derivatives have been shown to undergo highly stereoselective dicyclohexylboron chloride-mediated aldol reactions. After suitable synthetic manipulation of the resulting aldol adducts, chiral polyoxygenated molecules can be obtained in which either three or all four carbon atoms of the starting erythrulose molecule have been incorporated. Erythrulose derivatives may therefore behave, according to convenience, as chiral, functionalized d(3) or d(4) synthons. As an example, this methodology has been applied to a stereoselective synthesis of the naturally occurring, pharmacologically active lactone (+)-boronolide. (C) 2002 Elsevier Science Ltd. All rights reserved.