(3aS,4S,6R,6aR)-6-butyl-4-hydroxy-3a,4,6,6a-tetrahydrofuro[3,4-b]furan-2(3H)-one | 69681-89-6

• 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,4S,6R,6aR)-6-butyl-4-hydroxy-3a,4,6,6a-tetrahydrofuro[3,4-b]furan-2(3H)-one
• 英文别名: (3aS,4S,6R,6aR)-6-butyl-4-hydroxytetrahydrofuro[3,4-b]furan-2(3H)-one；(3aS,4S,6R,6aR)-6-butyl-4-hydroxy-3a,4,6,6a-tetrahydro-3H-furo[2,3-c]furan-2-one
• CAS: 69681-89-6
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: WHQYOOMWYLUDIS-WDQPUEAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  (3aS,4S,6R,6aR)-6-butyl-4-hydroxy-3a,4,6,6a-tetrahydrofuro[3,4-b]furan-2(3H)-one 在 jones reagent 作用下， 以 丙酮 为溶剂， 以91%的产率得到2-C-(carboxymethyl)-2,5-dideoxy-5-C-(n-propyl)-D-lyxono-1,4-lactone 2,3-γ-lactone
  参考文献：
  名称：

  对映纯双内酯的简单途径：Epi -nor-canadensolide，nor-canadensolide和canadensolide的两种对映异构体的合成

  摘要：

  已经开发了一种简单的策略，用于合成降钙假固体的对映异构体，epi-降钙假固体的对映异构体和candendensolide的中间体。由R -（+）-2,3-二-O-环己基丙三醛甘油制得的适当构造的烯丙醇衍生物的原酸酯克莱森重排，然后环氧化所得的不饱和酯产生羟基内酯，其在氧化时得到酮内酯。使用螯合控制或非螯合控制的方法选择性立体还原酮羰基导致天然或epi系列。极性基团之间的电子效应与酮内酯还原过程中β取代基的空间效应之间的相互作用被证明是决定立体化学结果的关键因素。羟基内酯的缩酮部分中潜在的醛官能团的再生提供了内酯，该内酯在氧化时产生了双内酯。

  DOI：

  10.1016/j.tet.2008.01.009
• 作为产物：
  描述：

  (4R,5R)-4-vinyl-5-[(R)-1-hydroxypentyl]-4,5-dihydro-2(3H)-furanone 在 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以96%的产率得到(3aS,4S,6R,6aR)-6-butyl-4-hydroxy-3a,4,6,6a-tetrahydrofuro[3,4-b]furan-2(3H)-one
  参考文献：
  名称：

  Chiral vicinal diols as platforms for separable diastereomers in Johnson–Claisen rearrangement: a new short route to (−)-nor-canadensolide, (−)-canadensolide and (−)-sporothriolide

  摘要：

  The chiral vicinal diols prepared by asymmetric dihydroxylation in high enantioselectivities provide an excellent platform for separable diastereomers in the Johnson-Claisen rearrangement. The separated syn-diastereomers were converted into the advanced gamma-(lactone-lactol) intermediates (in six steps, 26-27% overall yields) for the synthesis of (-)-nor-canadensoiide, (-)-canadensolide and (-)-sporothriolide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.084

文献信息

• A simple route to enantiopure bis-lactones: synthesis of both enantiomers of epi-nor-canadensolide, nor-canadensolide, and canadensolide
  作者：Sujit Mondal、Subrata Ghosh

  DOI：10.1016/j.tet.2008.01.009

  日期：2008.3

  A simple strategy has been developed for the synthesis of both enantiomers of nor-canadensolide, epi-nor-canadensolide, and an intermediate to canadensolide. An orthoester Claisen rearrangement of an appropriately constructed allyl alcohol derivative prepared from R-(+)-2,3-di-O-cyclohexylidine glyceraldehyde followed by epoxidation of the resulting unsaturated esters produced hydroxy-lactones, which

  已经开发了一种简单的策略，用于合成降钙假固体的对映异构体，epi-降钙假固体的对映异构体和candendensolide的中间体。由R -（+）-2,3-二-O-环己基丙三醛甘油制得的适当构造的烯丙醇衍生物的原酸酯克莱森重排，然后环氧化所得的不饱和酯产生羟基内酯，其在氧化时得到酮内酯。使用螯合控制或非螯合控制的方法选择性立体还原酮羰基导致天然或epi系列。极性基团之间的电子效应与酮内酯还原过程中β取代基的空间效应之间的相互作用被证明是决定立体化学结果的关键因素。羟基内酯的缩酮部分中潜在的醛官能团的再生提供了内酯，该内酯在氧化时产生了双内酯。
• Synthesis of β,γ-disubstituted-γ-lactones through a Johnson–Claisen rearrangement: a short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolide
  作者：Rodney A. Fernandes、Arun B. Ingle、Vijay P. Chavan

  DOI：10.1016/j.tetasy.2009.11.018

  日期：2009.12

  The Johnson-Claisen rearrangement of allyl alcohols with chiral vicinal diol functionality was employed to access chiral beta,gamma-disubstituted-gamma-lactones in high enantio- and diastereoselectivity. These were efficiently converted into nor-canadensolide, the advanced gamma-(lactone-lactol) intermediate for xylobovide, canadensolide and sporothriolide and the lactone moiety of the santolinolides. (C) 2009 Elsevier Ltd. All rights reserved.
• Chiral vicinal diols as platforms for separable diastereomers in Johnson–Claisen rearrangement: a new short route to (−)-nor-canadensolide, (−)-canadensolide and (−)-sporothriolide
  作者：Rodney A. Fernandes、Arun B. Ingle

  DOI：10.1016/j.tetlet.2008.12.084

  日期：2009.3

  The chiral vicinal diols prepared by asymmetric dihydroxylation in high enantioselectivities provide an excellent platform for separable diastereomers in the Johnson-Claisen rearrangement. The separated syn-diastereomers were converted into the advanced gamma-(lactone-lactol) intermediates (in six steps, 26-27% overall yields) for the synthesis of (-)-nor-canadensoiide, (-)-canadensolide and (-)-sporothriolide. (C) 2009 Elsevier Ltd. All rights reserved.