6-O-tert-butyldimethylsilyl-3,4-O-cyclohexylidene-D-altrono-1,5-lactone | 150496-22-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-tert-butyldimethylsilyl-3,4-O-cyclohexylidene-D-altrono-1,5-lactone
• CAS: 150496-22-3
• 化学式: C₁₈H₃₂O₆Si
• 分子量: 372.534
• InChiKey: MASUIMCBELPBPU-BARDWOONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-O-tert-butyldimethylsilyl-3,4-O-cyclohexylidene-D-altrono-1,5-lactone 在 吡啶 、 N-morpholine oxide 、 sodium azide 、 四丙基高钌酸铵 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.17h， 生成 (1S,4R,7R,8S)-1-amino-7,8-O-cyclohexylidene-7,8-dihydroxy-2,5-dioxa-bicyclo<2.2.2>octan-6-one
  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：

  2,3-O-1,1-环己烷二基-D-呋喃核糖 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-O-tert-butyldimethylsilyl-3,4-O-cyclohexylidene-D-altrono-1,5-lactone
  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

文献信息

• 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.
• 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.