S- ethanothioate | 16495-18-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: S- ethanothioate
• 英文别名: S-[[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl] ethanethioate
• CAS: 16495-18-4
• 化学式: C₈H₁₄O₃S
• 分子量: 190.263
• InChiKey: JKPQLSDXFXRAAN-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S- ethanothioate 在 sodium hydroxide 、 碘 作用下， 以 甲醇 为溶剂， 以82%的产率得到3,3'-dithiobis
  参考文献：
  名称：

  General Method for the Synthesis of Phospholipid Derivatives of 1,2-O-Diacyl-sn-Glycerols

  摘要：

  An efficient phosphite coupling protocol is described for the syntheses of the major classes of phospholipids that are derived from 1,2-O-diacyl-sn-glycerols and analogues thereof. The symmetrical diacyl glycerols 10c,d were prepared by straightforward acylation of 3-O-benzyl-sn-glycerol (7) with the appropriate carboxylic acid in the presence of dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMAP). A simple method for preparing saturated and unstaturated mixed 1,2-O-diacyl-sn-glycerols was then devised that involved stepwise acylation of 7 with different alkyl carboxylic acids and debenzylation this procedure is exemplified by the preparation of 10a,b. The 1,2-O-diacyl-sn-glycerols 10a-d were then coupled with suitably protected lipid head groups employing reactive alkyl or aryl dichlorophosphites to give intermediate phosphite triesters in high overall yields. Oxidation or sulfurization of these phosphites proceeded smoothly to give the corresponding phosphate or phosphorothioate triesters, deprotection of which then provided the phosphatidylcholines 16 and 17, the phosphatidylethanolamine 20, the phosphatidylserine 28, and the phosphatidylinositols 37 and 38. Preparation of 37 and 38 required the invention of an improved method for resolving the isopropylidene-protected D-myo-inositol derivative 33. This phosphite coupling procedure was modified to assemble phospholipids bearing-polyunsaturated acyl side chains at the sn-2-position as exemplified by the preparation of the phosphatidylethanolamine 26. The one-pot phosphite coupling procedure is also applicable to the syntheses of a variety of other biologically interesting phospholipid analogues. For example, the phosphatidylinositol analogues 49-51, in which the hydroxyl group at C(2) of the inositol ring has been modified, were prepared in excellent overall yields by conjoining the 1,2-O-diacyl-sn-glycerol 10c with the protected inositol derivatives 44, 45, and 48. Phospholipid analogues that contain other replacements of the phosphate group including phosphoramidates and thiophosphates maybe prepared as evidenced by the syntheses of 56 and 61 in which the sn-3 oxygen atom of the 1,2-O-diacyl-sn-glycerol moiety is replaced with an N-benzyl group or a sulfur atom, respectively.

  DOI：

  10.1021/jo00096a023
• 作为产物：
  描述：

  (S)-(+)-1,2-异亚丙基甘油 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 72.0h， 生成 S- ethanothioate
  参考文献：
  名称：

  通往新螺杂环的捷径：合成和结构研究

  摘要：

  我们开发了一种简短、高效和对映选择性合成的 1,4,7,10-四氧杂-和 1,7-二氧杂-4,10-二硫螺[5.5]十一烷。该方法涉及将 solketal 5 或硫醇衍生物 6 与 1,3-二氯丙酮 O-苄肟 (4) 反应，得到方便保护的对称酮 7 和 8。 所需的 4,10-二取代-1,7-二氧杂环己烷的制备[5.5]十一烷系统1和2需要在酸性介质中进行最终的“一锅”脱保护-螺环化过程。通过核磁共振光谱明确地确定了螺缩酮的结构和构型。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200600448

文献信息

• Pharmaceutical compositions containing thio-dioxolane derivatives having mucolytic activity
  申请人：PROTER S.p.A.

  公开号：EP0288871A2

  公开（公告）日：1988-11-02

  The present invention relates to pharmaceutical compositions contaning thiodioxolane derivatives having an interesting mucolytic activity, and to a process for the preparation of said thiodioxolane derivatives of the general structural formula in which the carbon atom marked with an asterisk indicates a asimmetry center in the molecule, X represents an hydroxy group or -SRʺ and Rʺ is hydrogen or a suitable acylic radical, R rapresents hydrogen, a lower alkyl, a lower hydroxy alkyl, or phenyl, Rʹ represents a lower alkyl, a lower hydroxy alkyl, phenyl, -(CH₂)nSRʺ where n is a whole number between 1 and 3 and Rʺ has the above indicated meaning, with condition that X and Rʹ can never be both type of groups.

  本发明涉及含有具有有趣的粘液溶解活性的硫代二氧杂环戊烷衍生物的药物组合物，以及制备上述硫代二氧杂环戊烷衍生物的工艺，其结构通式为 其中标有星号的碳原子表示分子中的一个相似中心、 X代表羟基或-SRʺ，Rʺ代表氢或合适的酰基、 R代表氢、低级烷基、低级羟基烷基或苯基、 Rʹ代表低级烷基、低级羟基烷基、苯基、-(CH₂)nSRʺ，其中 n 是介于 1 和 3 之间的整数，Rʺ 具有上述含义，条件是 X 和 Rʹ 绝不可以是两种类型的基团。
• US4910220A
  申请人：——

  公开号：US4910220A

  公开（公告）日：1990-03-20
• General Method for the Synthesis of Phospholipid Derivatives of 1,2-O-Diacyl-sn-Glycerols
  作者：Stephen F. Martin、John A. Josey、Yue-Ling Wong、Daniel W. Dean

  DOI：10.1021/jo00096a023

  日期：1994.8

  An efficient phosphite coupling protocol is described for the syntheses of the major classes of phospholipids that are derived from 1,2-O-diacyl-sn-glycerols and analogues thereof. The symmetrical diacyl glycerols 10c,d were prepared by straightforward acylation of 3-O-benzyl-sn-glycerol (7) with the appropriate carboxylic acid in the presence of dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMAP). A simple method for preparing saturated and unstaturated mixed 1,2-O-diacyl-sn-glycerols was then devised that involved stepwise acylation of 7 with different alkyl carboxylic acids and debenzylation this procedure is exemplified by the preparation of 10a,b. The 1,2-O-diacyl-sn-glycerols 10a-d were then coupled with suitably protected lipid head groups employing reactive alkyl or aryl dichlorophosphites to give intermediate phosphite triesters in high overall yields. Oxidation or sulfurization of these phosphites proceeded smoothly to give the corresponding phosphate or phosphorothioate triesters, deprotection of which then provided the phosphatidylcholines 16 and 17, the phosphatidylethanolamine 20, the phosphatidylserine 28, and the phosphatidylinositols 37 and 38. Preparation of 37 and 38 required the invention of an improved method for resolving the isopropylidene-protected D-myo-inositol derivative 33. This phosphite coupling procedure was modified to assemble phospholipids bearing-polyunsaturated acyl side chains at the sn-2-position as exemplified by the preparation of the phosphatidylethanolamine 26. The one-pot phosphite coupling procedure is also applicable to the syntheses of a variety of other biologically interesting phospholipid analogues. For example, the phosphatidylinositol analogues 49-51, in which the hydroxyl group at C(2) of the inositol ring has been modified, were prepared in excellent overall yields by conjoining the 1,2-O-diacyl-sn-glycerol 10c with the protected inositol derivatives 44, 45, and 48. Phospholipid analogues that contain other replacements of the phosphate group including phosphoramidates and thiophosphates maybe prepared as evidenced by the syntheses of 56 and 61 in which the sn-3 oxygen atom of the 1,2-O-diacyl-sn-glycerol moiety is replaced with an N-benzyl group or a sulfur atom, respectively.
• An Expedient Route to New Spiroheterocycles: Synthesis and Structural Studies
  作者：Marlène Goubert、Isabelle Canet、Marie-Eve Sinibaldi

  DOI：10.1002/ejoc.200600448

  日期：2006.11

  We have developed a short, efficient and enantioselective synthesis of 1,4,7,10-tetraoxa- and 1,7-dioxa-4,10-dithiaspiro[5.5]undecanes. The method involved the reaction of solketal 5 or thiol derivative 6 with 1,3-dichloropropanone O-benzyloxime (4) which affords the conveniently protected symmetrical ketones 7 and 8. Elaboration of the required 4,10-disubstituted-1,7-dioxaspiro[5.5]undecane systems

  我们开发了一种简短、高效和对映选择性合成的 1,4,7,10-四氧杂-和 1,7-二氧杂-4,10-二硫螺[5.5]十一烷。该方法涉及将 solketal 5 或硫醇衍生物 6 与 1,3-二氯丙酮 O-苄肟 (4) 反应，得到方便保护的对称酮 7 和 8。 所需的 4,10-二取代-1,7-二氧杂环己烷的制备[5.5]十一烷系统1和2需要在酸性介质中进行最终的“一锅”脱保护-螺环化过程。通过核磁共振光谱明确地确定了螺缩酮的结构和构型。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)