dibutyl (2-O-benzoyl-3-O-benzyl-5-O-tri-isopropylsilyl-α-D-arabinofuranosyl) phosphate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dibutyl (2-O-benzoyl-3-O-benzyl-5-O-tri-isopropylsilyl-α-D-arabinofuranosyl) phosphate
• 英文别名: [(2R,3S,4R,5R)-2-[dibutoxy(oxido)phosphaniumyl]oxy-4-phenylmethoxy-5-[tri(propan-2-yl)silyloxymethyl]oxolan-3-yl] benzoate
• 化学式: C₃₆H₅₇O₉PSi
• 分子量: 692.902
• InChiKey: FSUHVBNWKOBTPC-VYWROAQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  47
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  、 磷酸二丁酯 在 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以100%的产率得到dibutyl (2-O-benzoyl-3-O-benzyl-5-O-tri-isopropylsilyl-α-D-arabinofuranosyl) phosphate
  参考文献：
  名称：

  Synthesis of Glycosyl Phosphates from 1,2-Orthoesters and Application to in Situ Glycosylation Reactions

  摘要：

  A series of glycosyl phosphates were prepared in high yield by treatment of the corresponding 1,2-orthoesters with dibutyl phosphate. Glycosyl phosphates are efficient glycosylating agents even when used in crude form or when generated in situ. The immunodominant epitope trirhamnoside of group B Streptococcus was prepared to demonstrate the synthetic utility of the method.

  DOI：

  10.1021/ol0603155

文献信息

• Synthesis of Glycosyl Phosphates from 1,2-Orthoesters and Application to in Situ Glycosylation Reactions
  作者：Alessandra Ravidà、Xinyu Liu、Linda Kovacs、Peter H. Seeberger

  DOI：10.1021/ol0603155

  日期：2006.4.1

  A series of glycosyl phosphates were prepared in high yield by treatment of the corresponding 1,2-orthoesters with dibutyl phosphate. Glycosyl phosphates are efficient glycosylating agents even when used in crude form or when generated in situ. The immunodominant epitope trirhamnoside of group B Streptococcus was prepared to demonstrate the synthetic utility of the method.