[(2R,3R,4S,5S,6R)-4,5-diacetyloxy-6-[2-[diethoxy(oxido)phosphaniumyl]ethyl]-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate | 201854-53-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,5S,6R)-4,5-diacetyloxy-6-[2-[diethoxy(oxido)phosphaniumyl]ethyl]-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 201854-53-7
• 化学式: C₃₂H₄₉O₂₀P
• 分子量: 784.703
• InChiKey: PYBWAMHCXUQFCD-XTUBQRMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  53
• 可旋转键数：
  25
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  253
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5S,6R)-4,5-diacetyloxy-6-[2-[diethoxy(oxido)phosphaniumyl]ethyl]-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate 在 三甲基溴硅烷 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 {2-[(2R,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-ethyl}-phosphonic acid
  参考文献：
  名称：

  Diastereoselective synthesis of C-glycosylphosphonates via free-radical glycosylation

  摘要：

  A single step approach for the diastereoselective synthesis of C-glycosidic sugar phosphonates was developed by utilizing a free radical coupling to dialkyl vinylphosphonates to give the title compounds in moderate yield. The method is broadly applicable to sugars, deoxysugars, aminosugars, and oligosaccharides. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10498-1
• 作为产物：
  描述：

  乙烯基磷酸二乙酯 、 Acetic acid (3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-bromo-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 在 三正丁基氢锡 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以32%的产率得到[(2R,3R,4S,5S,6R)-4,5-diacetyloxy-6-[2-[diethoxy(oxido)phosphaniumyl]ethyl]-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  Diastereoselective synthesis of C-glycosylphosphonates via free-radical glycosylation

  摘要：

  A single step approach for the diastereoselective synthesis of C-glycosidic sugar phosphonates was developed by utilizing a free radical coupling to dialkyl vinylphosphonates to give the title compounds in moderate yield. The method is broadly applicable to sugars, deoxysugars, aminosugars, and oligosaccharides. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10498-1