monotetrabutylammonium 2-acetamido-2-deoxy-4,6-O-(di-tert-butylsilandiyl)-3-O-methyl-α-D-glucopyranosyl phosphate | 1092110-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: monotetrabutylammonium 2-acetamido-2-deoxy-4,6-O-(di-tert-butylsilandiyl)-3-O-methyl-α-D-glucopyranosyl phosphate
• 英文别名: [(4aR,6R,7R,8R,8aS)-7-acetamido-2,2-ditert-butyl-8-methoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl] hydrogen phosphate;tetrabutylazanium
• CAS: 1092110-75-2
• 化学式: C₁₆H₃₆N*C₁₇H₃₃NO₉PSi
• 分子量: 696.978
• InChiKey: JAFUKADFJSRIIZ-LGOICXCGSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  46
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  monotetrabutylammonium 2-acetamido-2-deoxy-4,6-O-(di-tert-butylsilandiyl)-3-O-methyl-α-D-glucopyranosyl phosphate 、 2',3'-di-O-acetyluridine-5'-O-yl(2-cyanoethoxy)(diisopropylamino)phosphane 在 4,5-二氰基咪唑 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 [(4aR,6R,7R,8R,8aS)-7-acetamido-2,2-ditert-butyl-8-methoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl] [2-cyanoethoxy-[[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphanyl] phosphate;tetrabutylazanium
  参考文献：
  名称：

  Synthesis of Sugar Nucleotides by Application of Phosphoramidites

  摘要：

  A new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate-phosphite intermediate Was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this one-pot procedure in good yields.

  DOI：

  10.1021/jo802021t
• 作为产物：
  描述：

  [(4aR,6R,7R,8R,8aS)-7-acetamido-2,2-ditert-butyl-8-methoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl] dibenzyl phosphate 、 四丁基氢氧化铵 在 10% Pd/C 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以99%的产率得到monotetrabutylammonium 2-acetamido-2-deoxy-4,6-O-(di-tert-butylsilandiyl)-3-O-methyl-α-D-glucopyranosyl phosphate
  参考文献：
  名称：

  Synthesis of Sugar Nucleotides by Application of Phosphoramidites

  摘要：

  A new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate-phosphite intermediate Was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this one-pot procedure in good yields.

  DOI：

  10.1021/jo802021t

文献信息

• Synthesis of Sugar Nucleotides by Application of Phosphoramidites
  作者：Henrik Gold、Pieter van Delft、Nico Meeuwenoord、Jeroen D. C. Codée、Dmitri V. Filippov、Gerrit Eggink、Herman S. Overkleeft、Gijs A. van der Marel

  DOI：10.1021/jo802021t

  日期：2008.12.5

  A new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate-phosphite intermediate Was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this one-pot procedure in good yields.