Sulfuric acid (3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester 2,2,2-trifluoro-ethyl ester | 197305-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Sulfuric acid (3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester 2,2,2-trifluoro-ethyl ester
• 英文别名: [(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methyl 2,2,2-trifluoroethyl sulfate
• CAS: 197305-65-0
• 化学式: C₁₄H₂₁F₃O₉S
• 分子量: 422.377
• InChiKey: NACNTHWUZAFTLR-ZKKRXERASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Sulfuric acid (3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester 2,2,2-trifluoro-ethyl ester 在 sodium azide 、 ammonium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 、 二氯甲烷 为溶剂， 以65%的产率得到
  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
• 作为产物：
  描述：

  双丙酮半乳糖 在 三氧化硫吡啶 、 柠檬酸 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 Sulfuric acid (3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester 2,2,2-trifluoro-ethyl ester
  参考文献：
  名称：

  硫酸酯保护基的开发

  摘要：

  研究了三氟乙基酯作为碳水化合物中硫酸盐单酯的保护基。该酯是由硫酸盐经三氟重氮乙烷处理而形成的，并且与碳水化合物化学中使用的其他常见保护基团相容。用叔丁醇钾选择性裂解三氟乙酯。

  DOI：

  10.1016/s0040-4039(97)01681-x

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.
• Development of a protecting group for sulfate esters
  作者：Andrew D. Proud、Jeremy C. Prodger、Sabine L. Flitsch

  DOI：10.1016/s0040-4039(97)01681-x

  日期：1997.10

  The trifuoroethyl ester was studied as a protection group for sulfate monoesters in carbohydrates. The ester was formed from the sulfate by treatment with trifluorodiazoethane and was compatible with other common protecting groups used in carbohydrate chemistry. Selective cleavage of the trifluoroethyl ester was achieved with potassium t-butoxide.

  研究了三氟乙基酯作为碳水化合物中硫酸盐单酯的保护基。该酯是由硫酸盐经三氟重氮乙烷处理而形成的，并且与碳水化合物化学中使用的其他常见保护基团相容。用叔丁醇钾选择性裂解三氟乙酯。