3-(2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl)propionitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl)propionitrile
• 英文别名: [(2R,3R,4R,5S,6R)-3,4,5-tribenzoyloxy-6-(2-cyanoethyl)oxan-2-yl]methyl benzoate
• 化学式: C₃₇H₃₁NO₉
• 分子量: 633.654
• InChiKey: ADXDMPPTKRSMCT-IZDBAANZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoylglucosyl bromide 、 丙烯腈 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.0h， 以16%的产率得到3-(2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl)propionitrile
  参考文献：
  名称：

  A highly stereoselective synthesis of α-linked C-glycopyranosides using 2,2′-azobis-(2,4-dimethyl-4-methoxyvaleronitrile) (V-70)

  摘要：

  alpha-linked C-glycopyranosides were obtained effectively by the radical addition reaction using V-70, an effective radical initiator under mild conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10259-3

文献信息

• A highly stereoselective synthesis of α-linked C-glycopyranosides using 2,2′-azobis-(2,4-dimethyl-4-methoxyvaleronitrile) (V-70)
  作者：Yasuyuki Kita、Kentoku Gotanda、Atsunori Sano、Masahisa Oka、Kenji Murata、Miki Suemura、Masato Matsugi

  DOI：10.1016/s0040-4039(97)10259-3

  日期：1997.12

  alpha-linked C-glycopyranosides were obtained effectively by the radical addition reaction using V-70, an effective radical initiator under mild conditions. (C) 1997 Elsevier Science Ltd.
• Efficient stereoselective synthesis of α-C-glycopyranosides using 2,2′-azobis(2,4-dimethyl-4-methoxyvaleronitrile) [V-70]
  作者：Kentoku Gotanda、Masato Matsugi、Miki Suemura、Chiyo Ohira、Atsunori Sano、Masahisa Oka、Yasuyuki Kita

  DOI：10.1016/s0040-4020(99)00587-6

  日期：1999.8

  Efficient synthesis of alpha-C-glycopyranosides through a radical addition reaction using 2.2'-azobis(2,4-dimethyl-4-methoxyvaleronitrile) [V-70] as an initiator under mild condition was developed. This method made it possible to completely control the stereocenter at the anomeric position and obtain only the alpha-anomer in high yield compared with AIBN, Et3B, and photo irradiation methods. (C) 1999 Elsevier Science Ltd. All rights reserved.