6-O-tert-butyldimethylsilyl-3,4-O-cyclohexylidene-2-O-trifluoromethanesulfonyl-D-altrono-1,5-lactone | 145372-71-0

• 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: 6-O-tert-butyldimethylsilyl-3,4-O-cyclohexylidene-2-O-trifluoromethanesulfonyl-D-altrono-1,5-lactone
• CAS: 145372-71-0
• 化学式: C₁₉H₃₁F₃O₈SSi
• 分子量: 504.597
• InChiKey: ASUBJUYICQTVKW-TUVASFSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  6-O-tert-butyldimethylsilyl-3,4-O-cyclohexylidene-2-O-trifluoromethanesulfonyl-D-altrono-1,5-lactone 在 N-morpholine oxide 、 sodium azide 、 四丙基高钌酸铵 、 potassium tert-butylate 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.84h， 生成 (-)-5-epi-hydantocidin
  参考文献：
  名称：

  Synthesis of 1-epihydantocidin from d-ribose

  摘要：

  A key step in a short synthesis of 1-epihydantocidin (2) is the unanticipated transformation of azidolactones (8) and (10) to a bicyclic amine (12) induced by tetra-n-propyl-ammonium perruthenate in the presence of morpholine-N-oxide. The structure of (12) was established by X-ray crystallographic analysis.

  DOI：

  10.1016/s0040-4039(00)73695-1
• 作为产物：
  描述：

  3,4-O-cyclohexylidene-D-altrono-1,5-lactone 在 吡啶 、 咪唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-O-tert-butyldimethylsilyl-3,4-O-cyclohexylidene-2-O-trifluoromethanesulfonyl-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

• 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。
• The ring contraction of δ-lactones with leaving group α-substituents: a strategy for the synthesis of 2,5-disubstituted highly functionalised homochiral tetrahydrofurans
  作者：Sik-Man S. Choi、Paul M. Myerscough、Antony J. Fairbanks、Ben M. Skead、Claire J. F. Bichard、Simon J. Mantell、Jong Chan Son、George W. J. Fleet、John Saunders、David Brown

  DOI：10.1039/c39920001605

  日期：——

  Treatment of derivatives of δ-lactones having a leaving group at C-2 with methanol in the presence of base gives methyl tetrahydrofuran-α-carboxylates in good to excellent yield with a high degree of stereocontrol of the carbon substituents at C-2 and C-5.

  在碱存在下，用甲醇处理C-2位带有保护基的γ-内酯衍生物，可以得到甲基四氢呋喃-γ-羧酸酯，收率良好到极佳，且C-2和C-5位碳取代基具有高度的立体选择性。
• Synthesis of 5- epi hydantocidin from D-ribose
  作者：Antony J. Fairbanks、George W.J. Fleet

  DOI：10.1016/0040-4020(95)00110-t

  日期：1995.3

  Tetra-n-propyl ammonium perruthenate in the presence of morpholine-N-oxide induced the unanticipated transformation of the epimeric alpha-azido-1,4-lactones 4 into the bicyclic amine 3 and provided the key step in the synthesis of 5-epihydantocidin 2. Brief investigations into the acid catalysed equilibration of hydantocidin 1 and 5-epihydantocidin 2 are described.