[(2R,4aR,6S,7R,8R,8aS)-7-hydroxy-2-phenyl-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 2,2,2-trifluoroethyl sulfate | 1269657-56-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,4aR,6S,7R,8R,8aS)-7-hydroxy-2-phenyl-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 2,2,2-trifluoroethyl sulfate
• CAS: 1269657-56-8
• 化学式: C₂₁H₂₁F₃O₈S₂
• 分子量: 522.52
• InChiKey: OCPXLLRYCQIABK-FFDFYAMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  TFE*OTf 、 (2R,6S,7R,8R,8aR)-2-phenyl-6-(phenylthio)hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol 在 1,2-二甲基咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 38.0h， 以91%的产率得到[(2R,4aR,6S,7R,8R,8aS)-7-hydroxy-2-phenyl-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 2,2,2-trifluoroethyl sulfate
  参考文献：
  名称：

  Preparation of trifluoroethyl- and phenyl-protected sulfates using sulfuryl imidazolium salts

  摘要：

  Sulfuryl imidazolium salts (SIS's), a new class of sulfating agents, were prepared bearing the trifluoroethyl (TFE) and phenyl groups, two functionalities that have been used for the protection of sulfate monoesters, by subjecting the corresponding sulfonyl imidazoles with methyl triflate. In contrast, SIS's bearing the electron donating neopentyl and isobutyl groups, two moieties that have also been used for the protection of sulfates, were found to be unstable and could not be isolated though SIS's bearing electron donating aryl groups, such as a p-methoxyphenyl or p-thiomethylphenyl group were readily prepared and are stable compounds. In most instances, TFE-protected phenolic and carbohydrate sulfates were obtained in good yield by reaction of the corresponding SIS's with steroids and carbohydrates. Phenyl-protected carbohydrates were also readily prepared using the corresponding SIS's. Those SIS's having a methyl group at the 2-position of the imidazole ring were, in general, superior sulfating agents to those, which lacked a methyl group at this position. The use of SIS's to prepare TFE-protected sulfates represents a significant improvement of the previous reported procedure, which involved treating unprotected sulfates with trifluorodiazoethane. The TFE protecting group was removed from steroidal sulfates and secondary sulfates in carbohydrates in high yields using NaN(3) in warm DMF, conditions that are less vigorous than those previously reported for removing this group. Deprotection of TFE-protected 6-sulfated carbohydrates using NaN3 in warm DMF proceeded in lower yields due to partial desulfation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.085

文献信息

• Preparation of trifluoroethyl- and phenyl-protected sulfates using sulfuryl imidazolium salts
  作者：Ahmed Y. Desoky、Jennifer Hendel、Laura Ingram、Scott Douglas Taylor

  DOI：10.1016/j.tet.2010.11.085

  日期：2011.2

  Sulfuryl imidazolium salts (SIS's), a new class of sulfating agents, were prepared bearing the trifluoroethyl (TFE) and phenyl groups, two functionalities that have been used for the protection of sulfate monoesters, by subjecting the corresponding sulfonyl imidazoles with methyl triflate. In contrast, SIS's bearing the electron donating neopentyl and isobutyl groups, two moieties that have also been used for the protection of sulfates, were found to be unstable and could not be isolated though SIS's bearing electron donating aryl groups, such as a p-methoxyphenyl or p-thiomethylphenyl group were readily prepared and are stable compounds. In most instances, TFE-protected phenolic and carbohydrate sulfates were obtained in good yield by reaction of the corresponding SIS's with steroids and carbohydrates. Phenyl-protected carbohydrates were also readily prepared using the corresponding SIS's. Those SIS's having a methyl group at the 2-position of the imidazole ring were, in general, superior sulfating agents to those, which lacked a methyl group at this position. The use of SIS's to prepare TFE-protected sulfates represents a significant improvement of the previous reported procedure, which involved treating unprotected sulfates with trifluorodiazoethane. The TFE protecting group was removed from steroidal sulfates and secondary sulfates in carbohydrates in high yields using NaN(3) in warm DMF, conditions that are less vigorous than those previously reported for removing this group. Deprotection of TFE-protected 6-sulfated carbohydrates using NaN3 in warm DMF proceeded in lower yields due to partial desulfation. (C) 2010 Elsevier Ltd. All rights reserved.