Acetic acid (2R,3S,4R,5S,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((E)-propenyl)-tetrahydro-pyran-4-yl ester | 578729-58-5

• 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-((E)-propenyl)-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3S,4R,5S,6R)-5-acetamido-3,4-diacetyloxy-6-[(E)-prop-1-enyl]oxan-2-yl]methyl acetate
• CAS: 578729-58-5
• 化学式: C₁₇H₂₅NO₈
• 分子量: 371.387
• InChiKey: RRZAVEAJUSDFOG-YGTIIVDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  乙烯 、 Acetic acid (2R,3S,4R,5S,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((E)-propenyl)-tetrahydro-pyran-4-yl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 96.0h， 以89%的产率得到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
• 作为产物：
  描述：

  3-(2'-acetamido-3',4',6-tri-O-acetyl-2'-deoxy-α-D-glucopyranosyl)-1-propene 在 1,5-cyclooctadiene-bis(Ph₂MeP)iridium(I)*hexafluorophosphate 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到Acetic acid (2R,3S,4R,5S,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((E)-propenyl)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Development of Co- and Post-Translational Synthetic Strategies to C-Neoglycopeptides

  摘要：

  [GRAPHICS]The synthesis of stable, C-linked analogues of glycopeptides is being investigated with two complementary synthetic strategies, co-translational and post-translational glycopeptide synthesis. The key feature of the present approach lies in an effective olefin cross-metathesis reaction that allows formation of both glycoamino acids and glycopeptides.

  DOI：

  10.1021/ol0264861

文献信息

• The preparation of C-glycosyl amino acids—an examination of olefin cross-metathesis
  作者：Frank W. Schmidtmann、Tyler E. Benedum、Glenn J. McGarvey

  DOI：10.1016/j.tetlet.2005.04.110

  日期：2005.7

  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.