Acetic acid (2R,3S,4R,5S,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-vinyl-tetrahydro-pyran-4-yl ester | 578729-62-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (2R,3S,4R,5S,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-vinyl-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3S,4R,5S,6R)-5-acetamido-3,4-diacetyloxy-6-ethenyloxan-2-yl]methyl acetate
• CAS: 578729-62-1
• 化学式: C₁₆H₂₃NO₈
• 分子量: 357.361
• InChiKey: SJLCAPKTIYIJER-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl N-benzyloxycarbonyl-L-allylglycinate 、 Acetic acid (2R,3S,4R,5S,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-vinyl-tetrahydro-pyran-4-yl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 反应 48.0h， 以77%的产率得到(E)-(S)-2-Benzyloxycarbonylamino-5-((2R,3S,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yl)-pent-4-enoic acid benzyl ester
  参考文献：
  名称：

  The preparation of C-glycosyl amino acids—an examination of olefin cross-metathesis

  摘要：

  A study investigating the structural features directing olefin cross-metathesis to afford C-glycoamino acids was carried out. These results lead to an appreciation of the importance of proximal functionality to the relative reactivity of olefins in metathesis reactions providing a variable that is useful to suppress undesirable self-metathesis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.110
• 作为产物：
  描述：

  5-acetamido-6,7,9-tri-O-acetyl-4,8-anhydro-1,2,3,5-tetradeoxy-D-glycero-D-ido-non-enitol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 (Ph₂Me)2IrCOD*PF₆ 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 116.0h， 生成 Acetic acid (2R,3S,4R,5S,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-vinyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of α- and β-C-glycosides of N-acetylglucosamine

  摘要：

  As part of efforts to make available new, classes of bioactive C-glycoconjugates, D-glucosamine has been effectively converted into a series of 2-deoxy-2-amino-C-glycosides. This versatile approach is keyed by a remarkably effective metal catalyzed olefin isomerization of the isomeric C-allyl amino sugars which, in turn, are readily available via radical allylation of D-glucosamine. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00818-9