(3aS,5S,6aS)-5-hydroxymethyl-perhydrofuro[3,2-b]furan-2-one | 391232-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: (3aS,5S,6aS)-5-hydroxymethyl-perhydrofuro[3,2-b]furan-2-one
• 英文别名: (3aS,5S,6aS)-5-hydroxymethyl-tetrahydro-furo[3,2-b]furan-2-one；(3aS,5S,6aS)-5-(hydroxymethyl)tetrahydrofuro[3,2-b]furan-2(3H)-one；(2S,3aS,6aS)-2-(hydroxymethyl)-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-5-one
• CAS: 391232-86-3
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: STYSQVNTUSKUHO-ZLUOBGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  叔丁基二苯基氯硅烷 、 (3aS,5S,6aS)-5-hydroxymethyl-perhydrofuro[3,2-b]furan-2-one 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以92%的产率得到(1S,5S,7S)-7-tert-butyldiphenylsilyloxymethyl-2,6-dioxabicyclo[3.3.0]octan-3-one
  参考文献：
  名称：

  Accessing tetrahydrofuran-based natural products by microbial Baeyer–Villiger biooxidation

  摘要：

  利用表达来自 Comamonas sp. NCIMB 9872 的环戊酮单加氧酶的重组全细胞，通过立体选择性 BaeyerâVilliger 生物氧化作用获得的杂环内酯，用于正式全合成含有四氢呋喃结构基团的各种天然产物。

  DOI：

  10.1039/b606633j
• 作为产物：
  描述：

  2,4-二溴-8-氧杂二环[3.2.1]辛-6-烯-3-酮 在 葡萄糖 、 碘 、 三正丁基氢锡 、 氯化铵 、 异丙基-beta-D-硫代半乳糖吡喃糖苷 、 β-环糊精 、 potassium iodide 、 potassium hydroxide 作用下， 以 aq. phosphate buffer 、 乙醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 208.0h， 生成 (3aS,5S,6aS)-5-hydroxymethyl-perhydrofuro[3,2-b]furan-2-one
  参考文献：
  名称：

  Synthesis of tetrahydrofuran-based natural products and their carba analogs via stereoselective enzyme mediated Baeyer–Villiger oxidation

  摘要：

  In this work we present efficient formal syntheses of several biologically interesting natural products (showdomycin, goniofufurone, tratts-kumausyne) and their novel carba analogs by applying different Baeyer-Villiger monooxygenases. This strategy provides access to tetrahydrofuran-based natural products, C-nucleosides and both antipodes of the corresponding carba analogs in high optical purities (up to >95% ee) starting from simple achiral and commercially available building blocks (tetrabromoacetone, furan and cyclopentadiene). The striking key features of this chemo-enzymatic approach are the introduction of four stereogenic centers in as few as three reaction steps within a desymmetrization approach and the short-cut of several reaction sequences by the implementation of a biocatalytic step. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.11.048

文献信息

• Accessing tetrahydrofuran-based natural products by microbial Baeyer–Villiger biooxidation
  作者：Marko D. Mihovilovic、Dario A. Bianchi、Florian Rudroff

  DOI：10.1039/b606633j

  日期：——

  A heterobicyclic lactone obtained by stereoselective Baeyer–Villiger biooxidation with recombinant whole-cells expressing cyclopentanone monooxygenase from Comamonas sp. NCIMB 9872 was used for formal total syntheses of various natural products containing a tetrahydrofuran structural motif.

  利用表达来自 Comamonas sp. NCIMB 9872 的环戊酮单加氧酶的重组全细胞，通过立体选择性 BaeyerâVilliger 生物氧化作用获得的杂环内酯，用于正式全合成含有四氢呋喃结构基团的各种天然产物。
• Efficient Palladium(II)-Mediated Construction of Functionalized Plakortone Cores
  作者：Gregory C. Paddon-Jones、Natasha L. Hungerford、Patricia Hayes、William Kitching

  DOI：10.1021/ol991055c

  日期：1999.12.1

  [GRAPHICS]Appropriate enediols experience a one-pot palladium(II)-mediated hydroxycyclization-carbonylation-lactonization sequence to provide sidechain-functionalized 2,6-dioxabicyclo[3.3.0]octan-3-ones, the core structures of the plakortones, a novel class of activators of cardiac SR-Ca2+-pumping ATPase, from the sponge Plakortis halichondrioides.
• Total Synthesis of (2<i>S</i>,3<i>S</i>,5<i>S</i>,10<i>S</i>)- 6,9-Epoxynonadec-18-ene-7,10-diol and Formal Total Synthesis of (+)-<i>trans</i>-Kumausyne from <scp>d</scp>-Arabinose
  作者：Rajendrakumar Reddy Gadikota、Christopher S. Callam、Todd L. Lowary

  DOI：10.1021/jo010830a

  日期：2001.12.1
• Synthesis of tetrahydrofuran-based natural products and their carba analogs via stereoselective enzyme mediated Baeyer–Villiger oxidation
  作者：Florian Rudroff、Dario A. Bianchi、Roberto Moran-Ramallal、Naseem Iqbal、Dominik Dreier、Marko D. Mihovilovic

  DOI：10.1016/j.tet.2015.11.048

  日期：2016.11

  In this work we present efficient formal syntheses of several biologically interesting natural products (showdomycin, goniofufurone, tratts-kumausyne) and their novel carba analogs by applying different Baeyer-Villiger monooxygenases. This strategy provides access to tetrahydrofuran-based natural products, C-nucleosides and both antipodes of the corresponding carba analogs in high optical purities (up to >95% ee) starting from simple achiral and commercially available building blocks (tetrabromoacetone, furan and cyclopentadiene). The striking key features of this chemo-enzymatic approach are the introduction of four stereogenic centers in as few as three reaction steps within a desymmetrization approach and the short-cut of several reaction sequences by the implementation of a biocatalytic step. (C) 2015 Elsevier Ltd. All rights reserved.