methyl 2,3,4,6-bis(di-O-isopropylidene)-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-pivaloyl)-α-D-glucopyranoside | 1008130-97-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4,6-bis(di-O-isopropylidene)-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-pivaloyl)-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-4,5-bis(2,2-dimethylpropanoyloxy)-6-methoxy-2-[[(1R,2S,6S,7S,9R)-4,4,12,12-tetramethyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecan-7-yl]oxymethyl]oxan-3-yl] 2,2-dimethylpropanoate
• CAS: 1008130-97-9
• 化学式: C₃₄H₅₆O₁₄
• 分子量: 688.81
• InChiKey: WIAWYKRMLSKNJI-BJIBAOMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  [(1R,2S,6S,7R,9R)-4,4,12,12-tetramethyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecan-7-yl] 2,2,2-trichloroethanimidate 、 (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate) 在 tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate) 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl 2,3,4,6-bis(di-O-isopropylidene)-D-mannopyranosyl-(1->6)-2,3,4-tri-O-pivaloyl)-α-D-glucopyranoside 、 methyl 2,3,4,6-bis(di-O-isopropylidene)-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-pivaloyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Cationic Palladium(II)-Catalyzed Stereoselective Glycosylation with Glycosyl Trichloroacetimidates

  摘要：

  [GRAPHICS]The development of a new method for stereoselective glycosylation with glycosyl trichloroacetimidate donors employing cationic palladium(II), Pd(CH3CN)(4)(BF4)(2), is described. This process employs Pd(CH3CN)(4)(BF4)(2) as an efficient activator, providing access to a variety of disaccharides and glycopeptides. This reaction is highly stereoselective and proceeds under mild conditions with low catalyst loading. Interestingly, this palladium catalysis directs beta-glucosylations in the absence of classical neighboring group participation.

  DOI：

  10.1021/jo702436p

文献信息

• Cationic Palladium(II)-Catalyzed Stereoselective Glycosylation with Glycosyl Trichloroacetimidates
  作者：Jaemoon Yang、Colleen Cooper-Vanosdell、Enoch A. Mensah、Hien M. Nguyen

  DOI：10.1021/jo702436p

  日期：2008.2.1

  [GRAPHICS]The development of a new method for stereoselective glycosylation with glycosyl trichloroacetimidate donors employing cationic palladium(II), Pd(CH3CN)(4)(BF4)(2), is described. This process employs Pd(CH3CN)(4)(BF4)(2) as an efficient activator, providing access to a variety of disaccharides and glycopeptides. This reaction is highly stereoselective and proceeds under mild conditions with low catalyst loading. Interestingly, this palladium catalysis directs beta-glucosylations in the absence of classical neighboring group participation.