[(2R,3R,4R,5R,6S)-4,5-diacetyloxy-3-[2-cyanoethoxy(phenylmethoxy)phosphoryl]oxy-6-methoxyoxan-2-yl]methyl acetate | 1200440-74-9

• 分子结构分类: 有机化合物
• 英文名称: [(2R,3R,4R,5R,6S)-4,5-diacetyloxy-3-[2-cyanoethoxy(phenylmethoxy)phosphoryl]oxy-6-methoxyoxan-2-yl]methyl acetate
• CAS: 1200440-74-9
• 化学式: C₂₃H₃₀NO₁₂P
• 分子量: 543.464
• InChiKey: RJDPHVYOOUXPSM-XRUWVLEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  166
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R,6S)-4,5-diacetyloxy-3-[2-cyanoethoxy(phenylmethoxy)phosphoryl]oxy-6-methoxyoxan-2-yl]methyl acetate 、 四丁基氢氧化铵 以 二氯甲烷 、 水 为溶剂， 以94%的产率得到benzyl [(2R,3R,4R,5R,6S)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-methoxyoxan-3-yl] phosphate;tetrabutylazanium
  参考文献：
  名称：

  Highly Stereoselective Synthesis of α-d-Mannopyranosyl Phosphosugars

  摘要：

  alpha-Mannopyranosyl phosphosugars are obtained in 61-90% yields from 4,6-O-benzylidene-protected mannosyl thio-glycosides bearing ester functionality in the 3-O-position by coupling reactions with ammonium salts of phosphosugars on activation with 1-benzenesulfinyl piperidine, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride. Due to the presence of the disarming ester group, only the formation of the alpha-isomer was observed.

  DOI：

  10.1021/jo902254w
• 作为产物：
  描述：

  O-benzyl-O-β-cyanoethyl-N,N-diisopropylphosphoramidite 、 甲基2,3,6-三-O-乙酰基吡喃己糖苷 在 benzimidazolium triflate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到[(2R,3R,4R,5R,6S)-4,5-diacetyloxy-3-[2-cyanoethoxy(phenylmethoxy)phosphoryl]oxy-6-methoxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  Highly Stereoselective Synthesis of α-d-Mannopyranosyl Phosphosugars

  摘要：

  alpha-Mannopyranosyl phosphosugars are obtained in 61-90% yields from 4,6-O-benzylidene-protected mannosyl thio-glycosides bearing ester functionality in the 3-O-position by coupling reactions with ammonium salts of phosphosugars on activation with 1-benzenesulfinyl piperidine, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride. Due to the presence of the disarming ester group, only the formation of the alpha-isomer was observed.

  DOI：

  10.1021/jo902254w