[(2R,3S,4R,5R,6S)-3,4,6-triacetyloxy-5-[[(2S,3R,4R,5S,6R)-2,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-3-yl]sulfamoylamino]oxan-2-yl]methyl acetate | 1185733-82-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4R,5R,6S)-3,4,6-triacetyloxy-5-[[(2S,3R,4R,5S,6R)-2,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-3-yl]sulfamoylamino]oxan-2-yl]methyl acetate
• CAS: 1185733-82-7
• 化学式: C₂₈H₄₀N₂O₂₀S
• 分子量: 756.693
• InChiKey: WMYRNWLKQNSOQS-AZMCGPKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  51
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  295
• 氢给体数：
  2
• 氢受体数：
  22

反应信息

• 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 、 2,2,2-三氯乙基氯磺酸酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到[(2R,3S,4R,5R,6S)-3,4,6-triacetyloxy-5-[[(2S,3R,4R,5S,6R)-2,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-3-yl]sulfamoylamino]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  O- and N-Sulfations of Carbohydrates Using Sulfuryl Imidazolium Salts

  摘要：

  A series of sulfuryl imidazolium salts (SISs) were prepared and examined as reagents for incorporating trichloroethyl-protected sulfate esters into carbohydrates. The SIS that contained a 1,2-dimethylimidazolium moiety (SIS 9) proved to be a superior sulfating compared to SISs bearing no alkyl groups or bulkier alkyl groups on the imidazolium ring. Difficult O-sulfations that required prolonged reaction times and a large excess of the SIS bearing a 1-methylimidazolium group (SIS 5) were achieved in high yield using less than half the amount of SIS 9 in less time. Certain N-sulfated compounds that were practically inaccessible using SIS 5 were obtained in excellent yield using SIS 9.

  DOI：

  10.1021/jo9014112