cyclohexyl 2,3,5-tri-O-benzyl-D-ribofuranoside | 191340-56-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexyl 2,3,5-tri-O-benzyl-D-ribofuranoside
• 英文别名: 1-O-cyclohexyl-2,3,5-tri-O-benzyl-D-ribofuranose
• CAS: 191340-56-4
• 化学式: C₃₂H₃₈O₅
• 分子量: 502.651
• InChiKey: DZVVPPSGHDFKFO-DKZWVQASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  37.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  9-[(2R,3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]purin-6-amine 、 环己醇 在 三氟甲烷磺酸甲酯 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以77%的产率得到cyclohexyl 2,3,5-tri-O-benzyl-D-ribofuranoside
  参考文献：
  名称：

  One-step syntheses of alkyl glycosides and alkyl-substituted DNA oligomers by chemoselective glycosidations using DNA bases

  摘要：

  The simple and practical synthesis of alkyl glycosides by novel chemoselective glycosidations using natural resources, DNA and RNA nucleosides, was realized, and the one-step synthesis of chemoselectively modified DNA oligomers using the glycosidation method was also demonstrated. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.12.049

文献信息

• Trityl Salt Catalyzed Stereoselective Glycosylation of Alcohols with 1-Hydroxyribofuranose
  作者：Hiromi Uchiro、Teruaki Mukaiyama

  DOI：10.1246/cl.1996.79

  日期：1996.1

  presence of a catalytic amount of several trityl salts, 2,3,5-tri-O-benzyl-D-ribofuranose smoothly reacted with alcohols to give various β-ribofuranosides in high yields with high stereoselectivity while reversed stereoselectivity was observed in the coexistence of lithium perchlolate.

  在催化量的几种三苯甲基盐的存在下，2,3,5-三-O-苄基-D-呋喃核糖与醇顺利反应，以高收率和高立体选择性得到各种β-呋喃核糖苷，同时观察到反向立体选择性高氯酸锂共存。
• Tin(II) Chloride Catalyzed Synthesis of Ribofuranosides
  作者：Naoyuki Shimomura、Masahiro Saitoh、Teruaki Mukaiyama

  DOI：10.1246/cl.1994.433

  日期：1994.3

  from 2,3,5-tri-O-benzyl-1-O-iodoacetyl-D-ribofuranose and trimethylsilylated nucleophiles such as 3β-cholestanyl trimethylsilyl ether and phenyl trimethylsilyl sulfide is efficiently promoted by tin(II) chloride under mild conditions. When allyltrimethylsilane, azidotrimethylsilane, etc., are used as nucleophiles, combined use of catalytic amounts of SnCl2 and SiCl4 also afforded the corresponding ribofuranosides

  锡 (II) 有效促进了由 2,3,5-三-O-苄基-1-O-碘乙酰基-D-呋喃核糖和三甲基甲硅烷基化亲核试剂如 3β-胆甾烷三甲基甲硅烷基醚和苯基三甲基甲硅烷基硫化物催化合成几种 D-呋喃核糖苷) 在温和条件下氯化。当烯丙基三甲基硅烷、叠氮基三甲基硅烷等用作亲核试剂时，催化量的 SnCl2 和 SiCl4 的组合使用也以良好的产率提供相应的呋喃核苷。
• Diphosphonium Salts as Effective Reagents for Stereoselective Synthesis of 1,2-<i>cis</i>-Ribofuranosides
  作者：Teruaki Mukaiyama、Shinji Suda

  DOI：10.1246/cl.1990.1143

  日期：1990.7

  1,2-cis-Ribofuranosides are stereoselectively synthesized in high yields directly from 1-hydroxy sugars and alcohols or trimethylsilylated nucleophiles by the use of diphosphonium salts as a condensation reagent.

  通过使用二鏻盐作为缩合试剂，可直接从 1- 羟基糖和醇或三甲基硅烷化亲核物高产率地立体选择性合成 1,2-顺式-芝糖苷。