(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 | 945219-40-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (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
• CAS: 945219-40-9
• 化学式: C₂₂H₂₈NO₉P
• 分子量: 481.439
• InChiKey: VMGOZJXNADKJDN-CGXUPHRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (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 、 [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-(dimethoxyphosphorylamino)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到[(2R,3S,4R,5R,6R)-6-[[(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-yl]oxy]-3,4-diacetyloxy-5-(dimethoxyphosphorylamino)oxan-2-yl]methyl acetate
  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 、 potassium carbonate 、 对甲苯磺酸 、 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 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.67h， 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

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.