3-(2',3',4',6'-tetra-O-pivaloyl-β-D-glucopyranosyl)-1-propene | 1072785-88-6

• 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: 3-(2',3',4',6'-tetra-O-pivaloyl-β-D-glucopyranosyl)-1-propene
• 英文别名: perpivalated β-C-allyl glucopyranoside；[(2R,3R,4R,5S,6S)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-prop-2-enyloxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 1072785-88-6
• 化学式: C₂₉H₄₈O₉
• 分子量: 540.695
• InChiKey: DTFDVKYMCQAZOX-QGLKVJOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3-(β-D-glucopyranosyl)-1-propene 、 三甲基乙酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 24.0h， 以296 mg的产率得到3-(2',3',4',6'-tetra-O-pivaloyl-β-D-glucopyranosyl)-1-propene
  参考文献：
  名称：

  Studies on the Stereoselective Synthesis of C-Allyl Glycosides

  摘要：

  An investigation was carried out to explore the use of sulfoxide donors as common precursors to stereoisomeric C-glycoconjugates of glycoprotein and glycolipid tumor antigens. A study focusing on the effects of reaction conditions and substrate structure on the stereoselectivity of allylation was carried out. Although conditions were realized to selectively afford alpha-allylation products in good to excellent yields, the search for conditions favoring beta-selectivity proved less successful.

  DOI：

  10.1021/ol801710s

文献信息

• [EN] PREPARATION OF GLYCOSYLATED AMINO ACIDS, PROTEINS AND PEPTIDES VIA OLEFIN METATHESIS REACTIONS<br/>[FR] PREPARATION D'ACIDES AMINES, DE PROTEINES ET DE PEPTIDES GLYCOSYLES AU MOYEN DE REACTIONS DE METATHESE D'OLEFINES
  申请人：ISIS INNOVATION

  公开号：WO2005000873A1

  公开（公告）日：2005-01-06

  A method for the preparation of a glycosylated amino acid, protein or peptide, the method comprising reacting an unprotected carbohydrate compound containing a carbon-carbon double bond with an amino acid, a protein or a peptide containing a side-chain carbon-carbon double bond under conditions whereby olefin metathesis occurs. Preferably the method takes place in a protic solvent, and the carbohydrate compound is an allyl or vinyl C-glycoside.
• Studies on the Stereoselective Synthesis of <i>C</i>-Allyl Glycosides
  作者：Glenn J. McGarvey、Christopher A. LeClair、Bahar A. Schmidtmann

  DOI：10.1021/ol801710s

  日期：2008.11.6

  An investigation was carried out to explore the use of sulfoxide donors as common precursors to stereoisomeric C-glycoconjugates of glycoprotein and glycolipid tumor antigens. A study focusing on the effects of reaction conditions and substrate structure on the stereoselectivity of allylation was carried out. Although conditions were realized to selectively afford alpha-allylation products in good to excellent yields, the search for conditions favoring beta-selectivity proved less successful.