[(2S,3S,4aR,5R,7S,8S,8aS)-2,3,7-trimethoxy-2,3-dimethyl-8-phenylmethoxy-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-5-yl]methyl benzyl phosphate;tetrabutylazanium | 1200440-89-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3S,4aR,5R,7S,8S,8aS)-2,3,7-trimethoxy-2,3-dimethyl-8-phenylmethoxy-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-5-yl]methyl benzyl phosphate;tetrabutylazanium
• CAS: 1200440-89-6
• 化学式: C₁₆H₃₆N*C₂₇H₃₆O₁₁P
• 分子量: 810.019
• InChiKey: FCTNMPRBUZXOGQ-FFRRAXGHSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  8.16
• 重原子数：
  56
• 可旋转键数：
  24
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2S,3S,4aR,5R,7S,8S,8aS)-2,3,7-trimethoxy-2,3-dimethyl-8-phenylmethoxy-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-5-yl]methyl 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66%的产率得到[(2R,4aR,6R,7S,8S,8aR)-6-[[(2S,3S,4aR,5R,7S,8S,8aS)-2,3,7-trimethoxy-2,3-dimethyl-8-phenylmethoxy-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-5-yl]methoxy-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：

  [(2S,3S,4aR,5R,7S,8S,8aS)-2,3,7-trimethoxy-2,3-dimethyl-8-phenylmethoxy-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-5-yl]methyl benzyl 2-cyanoethyl phosphate 、 四丁基氢氧化铵 以 二氯甲烷 、 水 为溶剂， 以95%的产率得到[(2S,3S,4aR,5R,7S,8S,8aS)-2,3,7-trimethoxy-2,3-dimethyl-8-phenylmethoxy-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-5-yl]methyl 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.