O-isopropenyl 2,3,4,6-tetra-O-pivaloyl-β-glucopyranoside | 161325-87-7

• 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: O-isopropenyl 2,3,4,6-tetra-O-pivaloyl-β-glucopyranoside
• 英文别名: isopropenyl 2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranoside；[(2R,3R,4S,5R,6S)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-prop-1-en-2-yloxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 161325-87-7
• 化学式: C₂₉H₄₈O₁₀
• 分子量: 556.694
• InChiKey: KQAWNYOVAAVELG-YMQHIKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  39
• 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：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  O-isopropenyl 2,3,4,6-tetra-O-pivaloyl-β-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  异丙烯基糖苷的糖基转移：一锅中通过异丙烯基和正戊烯基吡喃葡萄糖苷的选择性偶联合成三糖

  摘要：

  带有酯保护基的O-异丙烯基糖苷被各种亲电试剂活化为糖基供体。非对映体纯的β-糖苷产物以良好的产率形成。在O-戊-4-烯基2,3,4,6-四-O-苄基-β-存在下的O-异丙烯基2,3,4,6-四-O-新戊酰基-β-吡喃葡萄糖苷的选择性活化吡喃葡萄糖苷可以在一个罐中进行两个连续的糖基偶联，从而以25％的收率得到三糖。

  DOI：

  10.1016/0040-4039(94)88449-8
• 作为产物：
  描述：

  2,3,4,6-O-四特戊酰基-alpha-D-溴代吡喃葡萄糖 、 bis(acetonyl)mercury 以 氯仿 为溶剂， 反应 27.0h， 以72%的产率得到O-isopropenyl 2,3,4,6-tetra-O-pivaloyl-β-glucopyranoside
  参考文献：
  名称：

  The Chemistry of Isopropenyl Glycopyranosides. Transglycosylations and Other Reactions

  摘要：

  Various anomerically pure isopropenyl alpha- and beta-glycopyranosides have been synthesized and shown to undergo synthetically useful transglycosylation reactions with a variety of primary and secondary carbohydrate alcohols. Although stable when stored, isopropenyl glycosides are readily activated as glycosyl donors by a variety of electrophiles, including N-iodosuccinimide/triflic acid, trimethylsilyl triflate, and triflic anhydride. Under conditions that retard formation of the glycosyl cation, the reactivity of isopropenyl glycosides is diverted away from transglycosylation and toward electrophilic addition across the vinyl ether double bond.

  DOI：

  10.1021/jo960190p

文献信息

• The Chemistry of Isopropenyl Glycopyranosides. Transglycosylations and Other Reactions
  作者：H. Keith Chenault、Alfredo Castro、Laura F. Chafin、Jie Yang

  DOI：10.1021/jo960190p

  日期：1996.1.1

  Various anomerically pure isopropenyl alpha- and beta-glycopyranosides have been synthesized and shown to undergo synthetically useful transglycosylation reactions with a variety of primary and secondary carbohydrate alcohols. Although stable when stored, isopropenyl glycosides are readily activated as glycosyl donors by a variety of electrophiles, including N-iodosuccinimide/triflic acid, trimethylsilyl triflate, and triflic anhydride. Under conditions that retard formation of the glycosyl cation, the reactivity of isopropenyl glycosides is diverted away from transglycosylation and toward electrophilic addition across the vinyl ether double bond.
• Glycosyl transfer by isopropenyl glycosides: Trisaccharide synthesis in one pot by selective coupling of isopropenyl and n-pentenyl glycopyranosides
  作者：H.Keith Chenault、Alfredo Castro

  DOI：10.1016/0040-4039(94)88449-8

  日期：1994.12

  O-Isopropenyl glycosides bearing ester protecting groups are activated as glycosyl donors by a variety of electrophiles. Diastereomerically pure β-glycoside products are formed in good yields. Selective activation of O-isopropenyl 2,3,4,6-tetra-O-pivaloyl-β-glucopyranoside in the presence of O-pent-4-enyl 2,3,4,6-tetra-O-benzyl-β-glucopyranoside allows two successive glycosyl couplings to be performed

  带有酯保护基的O-异丙烯基糖苷被各种亲电试剂活化为糖基供体。非对映体纯的β-糖苷产物以良好的产率形成。在O-戊-4-烯基2,3,4,6-四-O-苄基-β-存在下的O-异丙烯基2,3,4,6-四-O-新戊酰基-β-吡喃葡萄糖苷的选择性活化吡喃葡萄糖苷可以在一个罐中进行两个连续的糖基偶联，从而以25％的收率得到三糖。