(3aS,6R,6aS)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-[(trimethylsilyl)ethynyl]tetrahydrofuro[3,4-d][1,3]dioxol-4-ol | 1190937-18-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,6R,6aS)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-[(trimethylsilyl)ethynyl]tetrahydrofuro[3,4-d][1,3]dioxol-4-ol
• CAS: 1190937-18-8
• 化学式: C₁₇H₂₈O₆Si
• 分子量: 356.491
• InChiKey: RQCPGYGSMCRZJM-NLIDSEJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3aS,6R,6aS)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-[(trimethylsilyl)ethynyl]tetrahydrofuro[3,4-d][1,3]dioxol-4-ol 在 cesium fluoride 、 水 作用下， 以 水 、 乙腈 为溶剂， 以86%的产率得到1-ethynyl-[2,3:5,6]-di-O-isopropylidene-D-manno-furanose
  参考文献：
  名称：

  An oxepinone route to carbohydrate based oxepines

  摘要：

  Oxepines are ring expanded analogs of glycals that can be used to prepare septanose carbohydrates. A route to carbohydrate based oxepines that utilizes oxepinones as a key intermediate has been developed. The oxepinone intermediates were prepared via an amine catalyzed cycloisomerization of furanose hemi-ketals. 1,2-Reduction of the oxepinones followed by acetylation provided the novel ring expanded enol ether products. Moderate diastereoselectivity was observed for the reduction based on the starting oxepinone. 1,4-Addition onto the oxepinones was also demonstrated. Overall, the syntheses reported here will allow for ready access to novel ring expanded carbohydrate analogs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.041
• 作为产物：
  描述：

  2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 在 正丁基锂 、 草酰氯 作用下， 以 四氢呋喃 、 二甲基亚砜 、 甲苯 为溶剂， 生成 (3aS,6R,6aS)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-[(trimethylsilyl)ethynyl]tetrahydrofuro[3,4-d][1,3]dioxol-4-ol 、 (3aS,6R,6aS)-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-[(trimethylsilyl)ethynyl]tetrahydrofuro[3,4-d][1,3]dioxol-4-ol
  参考文献：
  名称：

  C-Triazolyl β-d-furanosides as LpxC inhibitors: stereoselective synthesis and biological evaluation

  摘要：

  C-Triazolyl beta-D-furanosides 10a-f were synthesized in a stereocontrolled way, starting from n-mannose. In the key steps of the synthesis a diastereoselective reduction of hemiketal 14 and a Cu(I) catalyzed [3+2]-cycloaddition of central building block 18 with various azides were performed. The synthesized hydroxamic acids were tested for their inhibitory activity against LpxC, a Zn2+-dependent deacetylase playing an important role in the biosynthesis of lipid A and therefore representing an interesting target for the development of novel antibiotics against Gram-negative bacteria. The C-triazolyl glycosides 10a-f did not exhibit antibiotic activity. However, the described synthesis is a versatile way to access C-triazolyl beta-D-furanosides bearing all of their substituents at the same side of the tetrahydrofuran ring. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.07.016