dibutyl (2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl) phosphate | 208656-42-2

• 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-3,4,6-tri-O-benzyl-β-D-glucopyranosyl) phosphate
• 英文别名: [(2S,3R,4S,5R,6R)-2-dibutoxyphosphoryloxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
• CAS: 208656-42-2
• 化学式: C₄₂H₅₁O₁₀P
• 分子量: 746.835
• InChiKey: OYPIRRAWRFJKLN-LTQQSIIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  53
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 dibutyl (2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl) phosphate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以91%的产率得到methyl O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  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
• 作为产物：
  描述：

  磷酸二丁酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 生成 dibutyl (2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl) phosphate
  参考文献：
  名称：

  An Expeditious Route toStreptococciandEnterococciGlycolipidsViaRing-Opening of 1,2-Anhydrosugars with Protic Acids

  摘要：

  1,2-Anhydroglucose 6 reacts smoothly and with a high degree of stereoselectivity with a variety of carboxylic and phosphoric acids resulting in the formation of the predominantly beta-oriented 1-O-acyl and 1-O-phosphorylglucoses 7-17. This methodology has been successfully applied in the construction of glycolipids 1a,b. Ring-opening of the 1,2-anhydroglucose derivative 19 with benzoic acid furnished exclusively the beta-aligned key intermediate 20. Subsequent ICDT-assisted chemoselective alpha-glucosylation of 20 with thioethyl donor 21, followed by glycosidation of kojibiosyl benzoate 22 with glycerol acceptor 23 gave the fully protected alpha-diglucosyl glycerol derivative 25, which upon desilylation (-->28), acylation (-->29 or 30) and deprotection afforded the target glycolipids 1a-b in high overall yield.

  DOI：

  10.1080/07328309808002906