(1S,2S)-1-(tert-butyldimethylsilyloxymethyl)-1,2-O-isopropylidene-cyclohex-3-ene-1,2-diol | 1025063-36-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S)-1-(tert-butyldimethylsilyloxymethyl)-1,2-O-isopropylidene-cyclohex-3-ene-1,2-diol
• 英文别名: [(3aS,7aS)-2,2-dimethyl-5,7a-dihydro-4H-1,3-benzodioxol-3a-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 1025063-36-8
• 化学式: C₁₆H₃₀O₃Si
• 分子量: 298.498
• InChiKey: KSZYNAZXQITIAZ-BBRMVZONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S)-1-(tert-butyldimethylsilyloxymethyl)-1,2-O-isopropylidene-cyclohex-3-ene-1,2-diol 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 24.0h， 以99%的产率得到(1S,2S,3R,4R)-1-(tert-butyldimethylsilyloxymethyl)-1,2-O-isopropylidene-cyclohexane-1,2,3,4-tetraol
  参考文献：
  名称：

  Facile synthesis of 6a-carba-β-d-fructopyranose through an RCM approach

  摘要：

  A new synthetic approach toward 6a-carba-beta-D-fructopyranose, a non-nutritive sweetener related to topiramate, is described. This scheme uses 2-C-hydroxymethyl-L-erythrose acetonide as starting material and efficiently delivers the target compound applying an RCM protocol for the construction of the carbocycle ring. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.046
• 作为产物：
  描述：

  (3S,4S)-4-(tert-butyldimethylsilyloxymethyl)-3,4-O-isopropylidene-octa-1,7-diene-3,4-diol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以82%的产率得到(1S,2S)-1-(tert-butyldimethylsilyloxymethyl)-1,2-O-isopropylidene-cyclohex-3-ene-1,2-diol
  参考文献：
  名称：

  Facile synthesis of 6a-carba-β-d-fructopyranose through an RCM approach

  摘要：

  A new synthetic approach toward 6a-carba-beta-D-fructopyranose, a non-nutritive sweetener related to topiramate, is described. This scheme uses 2-C-hydroxymethyl-L-erythrose acetonide as starting material and efficiently delivers the target compound applying an RCM protocol for the construction of the carbocycle ring. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.046

文献信息

• Facile synthesis of 6a-carba-β-d-fructopyranose through an RCM approach
  作者：Sotirios M. Totokotsopoulos、Alexandros E. Koumbis、John K. Gallos

  DOI：10.1016/j.tet.2008.02.046

  日期：2008.4

  A new synthetic approach toward 6a-carba-beta-D-fructopyranose, a non-nutritive sweetener related to topiramate, is described. This scheme uses 2-C-hydroxymethyl-L-erythrose acetonide as starting material and efficiently delivers the target compound applying an RCM protocol for the construction of the carbocycle ring. (c) 2008 Elsevier Ltd. All rights reserved.