p-methoxyphenyl 3,4,6-tri-O-acetyl-2-N-dimethylphosphoryl-2-deoxy-β-D-glucopyranoside | 945219-31-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 3,4,6-tri-O-acetyl-2-N-dimethylphosphoryl-2-deoxy-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-3,4-diacetyloxy-5-[[dimethoxy(oxido)phosphaniumyl]amino]-6-(4-methoxyphenoxy)oxan-2-yl]methyl acetate
• CAS: 945219-31-8
• 化学式: C₂₁H₃₀NO₁₂P
• 分子量: 519.442
• InChiKey: BASFCNUDSAXNCI-PFAUGDHASA-N

物化性质

• 沸点：
  586.6±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  160
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 3,4,6-tri-O-acetyl-2-N-dimethylphosphoryl-2-deoxy-β-D-glucopyranoside 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (2R,4aR,6S,7R,8R,8aS)-7-(dimethoxyphosphorylamino)-6-(4-methoxyphenoxy)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
  参考文献：
  名称：

  N-Dimethylphosphoryl-protected glucosamine trichloroacetimidate as an effective glycosylation donor

  摘要：

  Glycosylation of a variety of alcohols with 3,4,6-tri-O-acetyl-2-N-dimethylphosphoryl-2-deoxy-alpha-D-glucopyranosyl trichloroacetimidate as a glycosyl donor provided the corresponding coupled products in high yields and good beta-selectivity. N-Dimethylphosphoryl-protection stayed stable under acidic and basic conditions for further elaboration of the glucosaminecontaining oligosaccharides. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.150
• 作为产物：
  描述：

  1,3,4,6-四-O-乙酰基-2-氨基-2-脱氧-Β-D-葡萄糖盐酸盐 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 氨 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.67h， 生成 p-methoxyphenyl 3,4,6-tri-O-acetyl-2-N-dimethylphosphoryl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  N-Dimethylphosphoryl-protected glucosamine trichloroacetimidate as an effective glycosylation donor

  摘要：

  Glycosylation of a variety of alcohols with 3,4,6-tri-O-acetyl-2-N-dimethylphosphoryl-2-deoxy-alpha-D-glucopyranosyl trichloroacetimidate as a glycosyl donor provided the corresponding coupled products in high yields and good beta-selectivity. N-Dimethylphosphoryl-protection stayed stable under acidic and basic conditions for further elaboration of the glucosaminecontaining oligosaccharides. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.150

文献信息

• N-Dimethylphosphoryl-protection in the efficient synthesis of glucosamine-containing oligosaccharides with alternate N-acyl substitutions
  作者：You Yang、Biao Yu

  DOI：10.1016/j.tetlet.2007.07.108

  日期：2007.9

  Ready transformation of N-dimethylphosphoryl-protection into the corresponding N-acyl derivatives (in the presence of acyl chlorides and DMAP in pyridine) provided an effective approach to the synthesis of glucosamine-containing oligosaccharides with alternate N-acyl substitutions. (C) 2007 Elsevier Ltd. All rights reserved.