N-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)benzimine N-oxide | 114987-90-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)benzimine N-oxide
• 英文别名: [(3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl](phenylmeth-(Z)-ylidene)amine N-oxide；N-[(3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1-phenylmethanimine oxide
• CAS: 114987-90-5
• 化学式: C₁₉H₂₅NO₆
• 分子量: 363.411
• InChiKey: OUHFCMIVIRIILV-GERXXLIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)benzimine N-oxide 在 对甲苯磺酸一水合物 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 40.0h， 生成 (R)-(4-fluorophenyl)-3-phenyl-1,2,4-oxadiazolidin-5-one
  参考文献：
  名称：

  1,2,4-恶二唑烷酮是构型稳定的手性结构单元。

  摘要：

  DOI：

  10.1002/anie.200461934
• 作为产物：
  描述：

  二氧化硅 在 盐酸羟胺 、 sodium acetate 、 phosphorus pentoxide 、 sodium sulfate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 127.0h， 生成 N-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)benzimine N-oxide
  参考文献：
  名称：

  ZnCl₂-Mediated Stereoselective Addition of Terminal Alkynes to d-(+)-Mannofuranosyl Nitrones

  摘要：

  An optimized process for the addition of terminal alkynes to chiral nitrones using ZnCl2 and NEt3 in toluene is reported. The new reaction protocol is facile to perform and cost-effective. The resulting optically active propargyl N-hydroxylamines are isolated in good to excellent yield and high diastereoselectivity.

  DOI：

  10.1021/ol052331s

文献信息

• First Synthesis of Optically Pure Propargylic N-Hydroxylamines by Direct, Highly Diastereoselective Addition of Terminal Alkynes to Nitrones We thank the ETH, Roche Research Foundation, the Swiss National Science Foundation, Merck, and Aventis for their generous support.
  作者：Roger Fässler、Doug E. Frantz、Jürg Oetiker、Erick M. Carreira

  DOI：10.1002/1521-3773(20020816)41:16<3054::aid-anie3054>3.0.co;2-b

  日期：2002.8.16
• The kinetic anomeric effect. Additions of nucleophiles and of dipolarophiles to N-glycosylnitrones and to N-pseudoglycosylnitrones
  作者：Rolf Huber、Andrea Vasella

  DOI：10.1016/s0040-4020(01)97582-9

  日期：1990.1
• A Facile Synthesis of Glycosyl Hydroxylamines
  作者：P. Merino、S. Franco、F. L. Merchan、T. Tejero

  DOI：10.1080/00397919708007074

  日期：1997.10.1

  Condensation of N-benzylhydroxylamine with furanoses and pyranoses in the presence of zinc dichloride leads to novel anomeric glycosyl hydroxylamines.
• 1,2,4-Oxadiazolidinones as Configurationally Stable Chiral Building Blocks
  作者：Tobias Ritter、Erick M. Carreira

  DOI：10.1002/anie.200461934

  日期：2005.1.28
• ZnCl₂-Mediated Stereoselective Addition of Terminal Alkynes to <scp>d</scp>-(+)-Mannofuranosyl Nitrones
  作者：Dana Topić、Patrick Aschwanden、Roger Fässler、Erick M. Carreira

  DOI：10.1021/ol052331s

  日期：2005.11.1

  An optimized process for the addition of terminal alkynes to chiral nitrones using ZnCl2 and NEt3 in toluene is reported. The new reaction protocol is facile to perform and cost-effective. The resulting optically active propargyl N-hydroxylamines are isolated in good to excellent yield and high diastereoselectivity.