[(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 | 1200440-77-2

• 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 2-cyanoethyl phosphate
• CAS: 1200440-77-2
• 化学式: C₃₀H₄₀NO₁₁P
• 分子量: 621.621
• InChiKey: IIOBOROKXPUQFY-IDKJOJFCSA-N

物化性质

• 沸点：
  700.4±60.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  12

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 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
• 作为产物：
  描述：

  O-benzyl-O-β-cyanoethyl-N,N-diisopropylphosphoramidite 、 ((2S,3S,4aR,5R,7S,8S,8aS)-8-Benzyloxy-2,3,7-trimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-5-yl)-methanol 在 benzimidazolium triflate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以86%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 2-cyanoethyl phosphate
  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.