1,2-O-di-acetyl-3,4,5-tri-O-benzyl-myo-inositol | 214850-01-8

• 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: 1,2-O-di-acetyl-3,4,5-tri-O-benzyl-myo-inositol
• CAS: 214850-01-8
• 化学式: C₃₁H₃₄O₈
• 分子量: 534.606
• InChiKey: JIACGILFOOANHH-AADAKZITSA-N

物化性质

• 沸点：
  635.354±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.253±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  100.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 1,2-O-di-acetyl-3,4,5-tri-O-benzyl-myo-inositol 在 吡啶 作用下， 反应 4.0h， 以89%的产率得到(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2R,3R,4R,5R,6S)-2,3-diacetoxy-4,5,6-tris-benzyloxy-cyclohexyl ester
  参考文献：
  名称：

  Practical synthesis of a differentially protected myo-inositol

  摘要：

  An enantiospecific synthesis of 3,4,5-tri-O-benzyl-6-O-triisopropylsilyl-D-myo-inositol from D-xylose is reported. The synthesis features a diastereofacially selective SmI2-promoted pinacol cyclization. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00302-4
• 作为产物：
  描述：

  (2S,3R,4S)-2,3,4-Tris-benzyloxy-hex-5-enal 在 吡啶 、 4-二甲氨基吡啶 、 samarium diiodide 、 2,3-二巯基丁二酸 、 四丁基氟化铵 、 臭氧 、 silver nitrate 、 溶剂黄146 、 magnesium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 1,2-O-di-acetyl-3,4,5-tri-O-benzyl-myo-inositol
  参考文献：
  名称：

  Practical synthesis of a differentially protected myo-inositol

  摘要：

  An enantiospecific synthesis of 3,4,5-tri-O-benzyl-6-O-triisopropylsilyl-D-myo-inositol from D-xylose is reported. The synthesis features a diastereofacially selective SmI2-promoted pinacol cyclization. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00302-4

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.