3-[(2S,3R,4S,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-ethynyloxolan-2-yl]oxyprop-1-ynyl-trimethylsilane | 221468-05-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(2S,3R,4S,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-ethynyloxolan-2-yl]oxyprop-1-ynyl-trimethylsilane
• CAS: 221468-05-9
• 化学式: C₃₁H₆₂O₅Si₄
• 分子量: 627.172
• InChiKey: KGIHTAHNFIIDSS-LIGWSQQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.41
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[(2S,3R,4S,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-ethynyloxolan-2-yl]oxyprop-1-ynyl-trimethylsilane 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到(S)-1-[(2R,3R,4S,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-ethynyl-tetrahydro-furan-2-yl]-prop-2-yn-1-ol
  参考文献：
  名称：

  Stereochemical features of the [1,2]-Wittig rearrangement of O-glycosides derived from D-galactono- and D-xylono-γ-lactones: A new approach to the core part of zaragozic acids

  摘要：

  The Wittig rearrangement of D-galactono-gamma-lactone derived beta-O-glycoside is shown to afford beta-C-glycoside (retention product), a potentially useful intermediate for zaragozic acid synthesis. By contrast, the rearrangement of the D-xylonolactone-derived counterpart was found to violate the retention principle to yield an inversion product as the major product. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00043-x
• 作为产物：
  描述：

  D-木糖酸-gamma-内酯 在 咪唑 、 montmorillonite K-10 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[(2S,3R,4S,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-ethynyloxolan-2-yl]oxyprop-1-ynyl-trimethylsilane
  参考文献：
  名称：

  Stereochemical features of the [1,2]-Wittig rearrangement of O-glycosides derived from D-galactono- and D-xylono-γ-lactones: A new approach to the core part of zaragozic acids

  摘要：

  The Wittig rearrangement of D-galactono-gamma-lactone derived beta-O-glycoside is shown to afford beta-C-glycoside (retention product), a potentially useful intermediate for zaragozic acid synthesis. By contrast, the rearrangement of the D-xylonolactone-derived counterpart was found to violate the retention principle to yield an inversion product as the major product. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00043-x