2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl cyanide | 49815-05-6

• 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: 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl cyanide
• 英文别名: 1-Cyan-2,3,4-tri-O-acetyl-α-L-Rha；[(2S,3S,4R,5S,6S)-4,5-diacetyloxy-6-cyano-2-methyloxan-3-yl] acetate
• CAS: 49815-05-6
• 化学式: C₁₃H₁₇NO₇
• 分子量: 299.28
• InChiKey: FZNCABDRPGXWPZ-YBJAMMKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  氰化钠 、 2,3,4-tri-O-acetyl-L-rhamnopyranosyl bromide 以 乙二醇二甲醚 为溶剂， 以10%的产率得到2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl cyanide
  参考文献：
  名称：

  Cyano-1 ceto-3 et -4 L-rhamnoses

  摘要：

  DOI：

  10.1016/s0040-4039(00)74533-3

文献信息

• Efficient stereocontrolled synthesis of C-glycosides using glycosyl donors substituted by propane 1,3-diyl phosphate as the leaving group
  作者：Gurdial Singh、Hariprasad Vankayalapati

  DOI：10.1016/s0957-4166(01)00305-6

  日期：2001.7

  a- and beta -Glycosyl cyanides, per-O-acetyl-1,2-O-1-cyanoethylidenes and C-allyl glycopyranosides were efficiently prepared by treatment of 2,3,4-tri-O-acetyl-alpha,beta -L-rhamno-, L-fuco- and 2,3,4,6-tetra-O-acetyl-alpha,beta -D-galactopyranosyl propane-1,3-diyl phosphates with trimethylsilyl cyanide (TMSCN) and allyltrimethylsilane in the presence of trimethylsilyl triflate (TMSOTf). Similarly 2,3,4,6-tetra-O-benzyl-alpha,beta -D-manno- and D-glucopyranosyl propane-1,3-diyl phosphates were employed in the synthesis of C-glycosides. (C) 2001 Elsevier Science Ltd. All rights reserved.