1,3,4-tri-O-acetyl-6-O-triphenylmethyl-2-desoxy-2-(p-methoxybenzylidene)amino-β-D-glucopyranose | 117991-55-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1,3,4-tri-O-acetyl-6-O-triphenylmethyl-2-desoxy-2-(p-methoxybenzylidene)amino-β-D-glucopyranose
• 英文别名: 1,3,4-tri-O-acetyl-6-O-(triphenylmethyl)-2-deoxy-2-p-methoxybenzylideneamino-D-glucopyranoside；[(2R,3S,4R,5R,6S)-4,6-diacetyloxy-5-[(4-methoxyphenyl)methylideneamino]-2-(trityloxymethyl)oxan-3-yl] acetate
• CAS: 117991-55-6
• 化学式: C₃₉H₃₉NO₉
• 分子量: 665.74
• InChiKey: IRHPHWQOFXHHOG-OHTWKVNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  49.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  118.95
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1,3,4-tri-O-acetyl-6-O-triphenylmethyl-2-desoxy-2-(p-methoxybenzylidene)amino-β-D-glucopyranose 在 吡啶 、 chromium(VI) oxide 、 盐酸 、 硫酸 、 氢溴酸 作用下， 以 甲醇 、 乙醚 、 水 、 溶剂黄146 、 丙酮 为溶剂， 25.0~130.0 ℃ 、5.33 kPa 条件下， 反应 40.0h， 生成 N⁹--N⁶-benzoyladenine
  参考文献：
  名称：

  Timoshchuk, V. A.; Kulinkovich, L. N., Journal of general chemistry of the USSR, 1988, vol. 58, # 5, p. 1019 - 1024

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 吡啶 、 sodium hydroxide 作用下， 反应 24.0h， 生成 1,3,4-tri-O-acetyl-6-O-triphenylmethyl-2-desoxy-2-(p-methoxybenzylidene)amino-β-D-glucopyranose
  参考文献：
  名称：

  Timoshchuk, V. A.; Kulinkovich, L. N., Journal of general chemistry of the USSR, 1988, vol. 58, # 5, p. 1019 - 1024

  摘要：

  DOI：

文献信息

• Stereoselective α-glycosylation of C(6)-hydroxyl myo-inositols via nickel catalysis—application to the synthesis of GPI anchor pseudo-oligosaccharides
  作者：Matthew S. McConnell、Enoch A. Mensah、Hien M. Nguyen

  DOI：10.1016/j.carres.2013.09.006

  日期：2013.11

  Glycosylphosphatidyl inositol (GPI) anchors play a key role in many eukaryotic biological pathways. Stereoselective synthesis of GPI anchor analogues have proven to be critical for probing the biosynthesis, structure, and biological properties of these compounds. Challenges that have emerged from these efforts include the preparation of the selectively protected myo-inositol building blocks and the stereoselective construction of glucosamine alpha-linked myo-inositol containing pseudodisaccharide units. Herein, we describe the effectiveness of the cationic nickel(II) catalyst, Ni(4-F-PhCN)(4)(OTf)(2), at promoting selective formation of 1,2-cis-2-amino glycosidic bonds between the C(2)-N-substituted benzylideneamino trihaloacetimidate donors and C(6)-hydroxyl myo-inositol acceptors. This catalytic coupling process allows rapid access to pseudosaccharides of GPI anchors in good yields and with excellent levels of a-selectivity (alpha:beta = 10:1-20:1). In stark contrast, activation of trichloroacetimidate donors containing the C(2)-N-substituted benzylidene group with TMSOTf and BF3.OEt2 provided the desired pseudodisaccharides as a 1: 1 mixture of alpha- and beta-isomers. (C) 2013 Elsevier Ltd. All rights reserved.