benzyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside | 1008131-05-2

• 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: benzyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
• 英文别名: 2,3,4,6-O-benzoyl-β-D-glucopyranosyl-(1→4)-2,3-isopropylidene-1-O-benzyl-α-L-rhamnopyranoside；[(2R,3R,4S,5R,6S)-6-[[(3aR,4R,6S,7S,7aR)-2,2,6-trimethyl-4-phenylmethoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 1008131-05-2
• 化学式: C₅₀H₄₈O₁₄
• 分子量: 872.923
• InChiKey: PFGIKNPMTAUHHS-YZWJJCPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  64
• 可旋转键数：
  18
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  161
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside 、 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 在 tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate) 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以89%的产率得到benzyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
  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.