[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] benzyl phosphate;tetrabutylazanium | 1200440-81-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] benzyl phosphate;tetrabutylazanium
• CAS: 1200440-81-8
• 化学式: C₁₆H₃₆N*C₁₉H₂₆O₉P
• 分子量: 671.852
• InChiKey: HHEZTZKJJPGBOW-UEVNDZIESA-M

计算性质

• 辛醇/水分配系数(LogP)：
  7.09
• 重原子数：
  46
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] benzyl phosphate;tetrabutylazanium 、 phenyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside 在 1-(苯基亚硫酰基)哌啶 、 三氟甲磺酸酐 、 2,4,6-三叔丁基嘧啶 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到[(2R,4aR,6R,7S,8S,8aR)-6-[[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxy-phenylmethoxyphosphoryl]oxy-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 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
• 作为产物：
  描述：

  [(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] benzyl 2-cyanoethyl phosphate 、 四丁基氢氧化铵 以 二氯甲烷 、 水 为溶剂， 以100%的产率得到[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] benzyl 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

文献信息

• Highly Stereoselective Synthesis of α-<scp>d</scp>-Mannopyranosyl Phosphosugars
  作者：David Crich、Sébastien Picard

  DOI：10.1021/jo902254w

  日期：2009.12.18

  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.