1,2:5,6-diisopropylidene-α-D-glucofuranose 3-sulfate sodium salt | 108540-91-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:5,6-diisopropylidene-α-D-glucofuranose 3-sulfate sodium salt
• 英文别名: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose-3-sulfate sodium salt；O¹,O²;O⁵,O⁶-diisopropylidene-O³-sulfo-α-D-glucofuranose; sodium-salt；O¹,O²;O⁵,O⁶-Diisopropyliden-O³-sulfo-α-D-glucofuranose; Natrium-Salz；sodium;[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] sulfate
• CAS: 108540-91-6
• 化学式: C₁₂H₁₉O₉S*Na
• 分子量: 362.333
• InChiKey: CIRGWAMKROJUIE-SEAWRNJESA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.14
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 3-(ethylsulfite) 在 ruthenium trichloride sodium periodate 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 1.0h， 生成 1,2:5,6-diisopropylidene-α-D-glucofuranose 3-sulfate sodium salt
  参考文献：
  名称：

  硫酸盐制备的硫酸化氧化方案

  摘要：

  通过亚硫酸盐和硫酸盐二酯中间体，已经开发了一种新颖的高产率的醇硫酸化方法。亚硫酸盐二酯可用作通用的硫酸盐单酯前体，从而使后者化合物难以或不可能进行转化。

  DOI：

  10.1021/jo060404v

文献信息

• A Comprehensive Approach to the Synthesis of Sulfate Esters
  作者：Levi S. Simpson、Theodore S. Widlanski

  DOI：10.1021/ja056086j

  日期：2006.2.1

  approach to the synthesis of sulfate esters was developed. This approach permits the direct and high-yielding synthesis of protected sulfate monoesters. Subsequent deblocking to reveal sulfate monoesters is accomplished in near-quantitative yield. The exceptionally stable neopentyl protecting group and the labile isobutyl protecting group were utilized in the synthesis of aromatic and aliphatic sulfate

  开发了合成硫酸酯的综合方法。这种方法允许直接和高产率合成受保护的硫酸单酯。随后解封以显示硫酸单酯以接近定量的产率完成。异常稳定的新戊基保护基团和不稳定的异丁基保护基团用于合成芳香族和脂肪族硫酸单酯。还探索和开发了调整保护基团反应性的策略。
• 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.
• A Sulfitylation−Oxidation Protocol for the Preparation of Sulfates
  作者：M. Huibers、Álvaro Manuzi、Floris P. J. T. Rutjes、Floris L. van Delft

  DOI：10.1021/jo060404v

  日期：2006.9.1

  A novel, high-yielding method for sulfation of alcohols has been developed, proceeding via sulfite- and sulfate diester intermediates. Sulfite diesters serve as versatile sulfate monoester precursors, allowing for transformations that are difficult or impossible with the latter compounds.

  通过亚硫酸盐和硫酸盐二酯中间体，已经开发了一种新颖的高产率的醇硫酸化方法。亚硫酸盐二酯可用作通用的硫酸盐单酯前体，从而使后者化合物难以或不可能进行转化。