1-O-(Boc-L-Ser)-2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside | 1008131-03-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-O-(Boc-L-Ser)-2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-2-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
• CAS: 1008131-03-0
• 化学式: C₄₃H₄₉NO₁₁
• 分子量: 755.862
• InChiKey: LDFQTOUAPYLEBV-GNCYQCACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  55
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 、 Boc-L-丝氨酸甲酯 在 tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate) 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以92%的产率得到1-O-(Boc-L-Ser)-2-O-benzoyl-3,4,6-tri-O-benzyl-β-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.