1-O-acetyl-2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranose | 178403-57-1

• 英文名称: 1-O-acetyl-2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranose
• 英文别名: pivaloyl(-2)[pivaloyl(-3)][pivaloyl(-4)][pivaloyl(-6)]a-Glc1Ac；[(2R,3R,4S,5R,6R)-6-acetyloxy-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 178403-57-1
• 化学式: C₂₈H₄₆O₁₁
• 分子量: 558.667
• InChiKey: AUNFCWKXZIWWJR-OBKDMQGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranose 在 N-碘代丁二酰亚胺 、 dimethyltitanocene 、 三氟甲磺酸 、 4 Angstroem MS 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 15.08h， 生成 [(2R,3R,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-[1-iodo-2-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]propan-2-yl]oxyoxan-2-yl]methyl 2,2-dimethylpropanoate
  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
• 作为产物：
  描述：

  乙酸酐 、 (2S,3R,4S,5R,6R)-6-((新戊酰氧基)甲基)四氢-2H-吡喃-2,3,4,5-四 在 硫酸 作用下， 反应 1.0h， 以60%的产率得到1-O-acetyl-2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranose
  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

• Hydrolysis of O-Isopropenyl Glucopyranosides Involves C-Protonation and Alkenyl Ether Cleavage and Exhibits a Kinetic Influence of Anomeric Configuration
  作者：H. Keith Chenault、Laura F. Chafin

  DOI：10.1021/jo00100a015

  日期：1994.10

  Hydrolysis of O-isopropenyl alpha-glucopyranoside occurs by C-protonation and alkenyl ether (not glycosidic) C-O bond cleavage and proceeds in 10 mM salicylate buffer, at pH 3.0 and 25 degrees C, 4.5 times faster than the similar hydrolysis of its beta anomer.