2,6-Anhydro-3,4-O-cyclohexylidene-D-altrono-1,5-lactone | 156943-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 2,6-Anhydro-3,4-O-cyclohexylidene-D-altrono-1,5-lactone
• 英文别名: (1S,2R,6R,7R)-spiro[3,5,8,10-tetraoxatricyclo[5.2.2.02,6]undecane-4,1'-cyclohexane]-9-one
• CAS: 156943-96-3
• 化学式: C₁₂H₁₆O₅
• 分子量: 240.256
• InChiKey: AJZNXMVDWYDWIW-KYXWUPHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-Anhydro-3,4-O-cyclohexylidene-D-altrono-1,5-lactone 在 锂硼氢 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 生成 1,5-anhydro-D-talitol
  参考文献：
  名称：

  由糖内酯合成四氢吡喃

  摘要：

  γ-和δ-己内酯的脱水，可以通过在C-2处的三氟甲磺酸酯离去基团的分子内亲核置换，或通过OH-6的Mitsunobu型置换来实现，可以得到含有四氢吡喃环的双环内酯。这些双环内酯的还原或亲核开环以良好的产率提供了多官能化的四氢吡喃。

  DOI：

  10.1016/s0040-4020(98)00837-0
• 作为产物：
  描述：

  6-O-tert-butyldimethylsilyl-3,4-O-cyclohexylidene-2-O-trifluoromethanesulfonyl-D-altrono-1,5-lactone 在 sodium acetate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 2,6-Anhydro-3,4-O-cyclohexylidene-D-altrono-1,5-lactone
  参考文献：
  名称：

  Tetrahydropyran derivatives from γ- and δ-hexonolactones

  摘要：

  Both delta- and gamma-hexonolactones provide templates for the construction of bicyclic lactones in which a new tetrahydropyran ring has been formed from overall elimination of water from the C-2 and C-6 hydroxyl groups. Such studies may provide a strategy for the synthesis of C-glycosides from elimination of water between C-2 and C-6 of heptonolactones.

  DOI：

  10.1016/s0040-4039(00)76908-5

文献信息

• Tetrahydrofuran amino acids: Secondary structure in tetrameric and octameric carbopeptoids derived from a D-allo 5-(aminomethyl)tetrahydrofuran-2-carboxylic acid
  作者：Natasha L. Hungerford、Timothy D. W. Claridge、Mark P. Watterson、Robin T. Aplin、Andres Moreno、George W. J. Fleet

  DOI：10.1039/b002996n

  日期：——

  The synthesis of a D-allo-5-(azidomethyl)tetrahydrofuran-2-carboxylate as an amino acid precursor (in which the carboxylic acid is cis to the azidomethyl substituent and trans to the diol moiety) is reported from D-ribose. The oligomerisation of this monomer to dimeric, tetrameric and octameric carbopeptoids is described. NMR studies into the solution structures of cyclohexylidene-protected oligomers and of a deprotected tetramer with eight free hydroxy groups are described.

  报道了一种D-allo-5-(叠氮甲基)四氢呋喃-2-羧酸酯的合成，该化合物作为氨基酸前驱体（其羧酸与叠氮甲基取代基为顺式，与二醇部分为反式）。文中描述了该单体的寡聚化，生成二聚体、四聚体和八聚体的碳肽类化合物。同时，对环己烯基保护的寡聚体和一个解保护的四聚体（具有八个自由羟基）在溶液中的结构进行了NMR研究。
• Synthesis of tetrahydropyrans from sugar lactones
  作者：Juan C. Estevez、Antony J. Fairbanks、George W.J. Fleet

  DOI：10.1016/s0040-4020(98)00837-0

  日期：1998.10

  Dehydration of both γ- and δ- hexonolactones, either by intramolecular nucleophilic displacement of triflate leaving groups at C-2, or by Mitsunobu type displacement of the OH-6, provides access to bicyclic lactones which contain tetrahydropyran rings. Reduction or nucleophilic ring opening of these bicyclic lactones furnishes polyfunctionalised tetrahydropyrans in good yield.

  γ-和δ-己内酯的脱水，可以通过在C-2处的三氟甲磺酸酯离去基团的分子内亲核置换，或通过OH-6的Mitsunobu型置换来实现，可以得到含有四氢吡喃环的双环内酯。这些双环内酯的还原或亲核开环以良好的产率提供了多官能化的四氢吡喃。
• Tetrahydropyran derivatives from γ- and δ-hexonolactones
  作者：Juan C. Estevez、Antony J. Fairbanks、Kenneth Y. Hsia、Peter Ward、George W.J. Fleet

  DOI：10.1016/s0040-4039(00)76908-5

  日期：1994.5

  Both delta- and gamma-hexonolactones provide templates for the construction of bicyclic lactones in which a new tetrahydropyran ring has been formed from overall elimination of water from the C-2 and C-6 hydroxyl groups. Such studies may provide a strategy for the synthesis of C-glycosides from elimination of water between C-2 and C-6 of heptonolactones.