ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)-2-(ethoxycarbonyl)acetate | 119366-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)-2-(ethoxycarbonyl)acetate
• 英文别名: diethyl 2-[(2R,3S,6S)-3-phenylmethoxy-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-6-yl]propanedioate
• CAS: 119366-97-1
• 化学式: C₂₇H₃₂O₇
• 分子量: 468.547
• InChiKey: NRBYLCIAEFJRJZ-KMDXXIMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)-2-(ethoxycarbonyl)acetate 在 palladium on activated charcoal 氢气 作用下， 生成 2-((2S,5S,6R)-5-Hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-malonic acid diethyl ester
  参考文献：
  名称：

  Differentiation of anomericC-glycosides by mass spectrometry using fast atom bombardment, mass-analysed ion kinetic energy and collision-activated dissociation

  摘要：

  AbstractPositive‐ion fast atom bombardment mass spectrometry appears to be a useful method for the differentiation of anomeric C‐glycosides. The mass‐analysed ion kinetic energy (MIKE) and collision‐activated dissociation (CAD) MIKE spectra of selected positive ions can be used as fingerprints of the α‐ or β‐anomers. The main fragmentation routes and particularly the formation of the [M − H]+ ion and the [M + H − PhCH2OH]+ ion were traced for each anomer.

  DOI：

  10.1002/oms.1210270328
• 作为产物：
  描述：

  Acetic acid (2R,3S,6R)-2-acetoxymethyl-6-phenoxy-3,6-dihydro-2H-pyran-3-yl ester 在 氢氧化钾 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 、 1,4-双(二苯基膦)丁烷 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 甲醇 、 二甲基亚砜 、 甲苯 、 乙腈 为溶剂， 反应 19.25h， 生成 ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)-2-(ethoxycarbonyl)acetate
  参考文献：
  名称：

  Palladium(0)-based approach to functionalized C-glycopyranosides

  摘要：

  DOI：

  10.1021/jo00269a026

文献信息

• BRAKTA, MOHAMED;LHOSTE, PAUL;SINOU, DENIS, J. ORG. CHEM., 54,(1989) N, C. 1890-1896
  作者：BRAKTA, MOHAMED、LHOSTE, PAUL、SINOU, DENIS

  DOI：——

  日期：——
• Palladium(0)-based approach to functionalized C-glycopyranosides
  作者：Mohamed Brakta、Paul Lhoste、Denis Sinou

  DOI：10.1021/jo00269a026

  日期：1989.4
• Differentiation of anomericC-glycosides by mass spectrometry using fast atom bombardment, mass-analysed ion kinetic energy and collision-activated dissociation
  作者：Mohamed Brakta、Brahim Chaguir、Denis Sinou、Joseph Banoub、Michel Becchi

  DOI：10.1002/oms.1210270328

  日期：1992.3

  AbstractPositive‐ion fast atom bombardment mass spectrometry appears to be a useful method for the differentiation of anomeric C‐glycosides. The mass‐analysed ion kinetic energy (MIKE) and collision‐activated dissociation (CAD) MIKE spectra of selected positive ions can be used as fingerprints of the α‐ or β‐anomers. The main fragmentation routes and particularly the formation of the [M − H]+ ion and the [M + H − PhCH2OH]+ ion were traced for each anomer.