methyl 4-O-tert-butyldimethylsilyl-2,3-di-O-isopropylidene-α-L-rhamnopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside | 1008131-00-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-tert-butyldimethylsilyl-2,3-di-O-isopropylidene-α-L-rhamnopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-2-[[(3aR,4R,6S,7S,7aS)-7-[tert-butyl(dimethyl)silyl]oxy-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]oxymethyl]-4,5-dibenzoyloxy-6-methoxyoxan-3-yl] benzoate
• CAS: 1008131-00-7
• 化学式: C₄₃H₅₄O₁₃Si
• 分子量: 806.979
• InChiKey: HVOSSGRMZHLHHV-FKIKKVBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.71
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  甲基2,3,4-三-O-苯甲酰-α-D-吡喃葡萄糖苷 、 [(3aR,4S,6S,7S,7aS)-7-[tert-butyl(dimethyl)silyl]oxy-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl] 2,2,2-trichloroethanimidate 在 tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate) 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以70%的产率得到methyl 4-O-tert-butyldimethylsilyl-2,3-di-O-isopropylidene-α-L-rhamnopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-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.