3,3'-dithiobis | 69161-83-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3'-dithiobis
• 英文别名: (R,R)-bis(2,2-dimethyl-1,3-dioxolanylmethyl)disulfide；3,3'-dithiobis(O-1,2-isopropylidene-1,2(S)-propanediol)；(4R)-4-[[[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyldisulfanyl]methyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 69161-83-7
• 化学式: C₁₂H₂₂O₄S₂
• 分子量: 294.436
• InChiKey: DZZIERXVBQNAPV-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  87.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,3'-dithiobis 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 以96%的产率得到3,3'-dithiobis<1,2(S)-propanediol>
  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：

  (R)-(-)-对甲基苯磺酸-2,2-二甲基-1,3-二氧戊环基-4-甲酯 在 三乙基硼氢化锂 、 sulfur 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以42%的产率得到3,3'-dithiobis
  参考文献：
  名称：

  对映体纯的双（2,2-二甲基-1,3-二氧戊环）硫属化物和二硫属化物的合成†

  摘要：

  在这里，我们描述了硫属元素（硫，硒和碲）的亲核物种与（R）-和（S）-Solketal甲苯磺酸盐之间的反应，以较短的反应时间和良好的制备对映体纯的bis-1,3-dioxolanylmethyl硫属元素化物和二硫属元素化物。产量。此外，在与丙烯腈的迈克尔反应中评估了新的二硒化物4a，在两步之后得到（R）-3-[（2,3-二羟丙基）硒基]丙烷腈6b。

  DOI：

  10.1039/c5nj02945g

文献信息

• 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.
• Synthesis of enantiomerically pure bis(2,2-dimethyl-1,3-dioxolanylmethyl)chalcogenides and dichalcogenides
  作者：Elton L. Borges、Thiago J. Peglow、Márcio S. Silva、Caroline G. Jacoby、Paulo H. Schneider、Eder J. Lenardão、Raquel G. Jacob、Gelson Perin

  DOI：10.1039/c5nj02945g

  日期：——

  Herein we describe the reaction between the nucleophilic species of chalcogenium (sulfur, selenium and tellurium) and (R)- and (S)-solketal tosylates to prepare enantiomerically pure bis-1,3-dioxolanylmethyl chalcogenides and dichalcogenides in short reaction times and good yields. Furthermore, the new diselenide 4a was evaluated in the Michael reaction with acrylonitrile, giving (R)-3-[(2,3-dihyd

  在这里，我们描述了硫属元素（硫，硒和碲）的亲核物种与（R）-和（S）-Solketal甲苯磺酸盐之间的反应，以较短的反应时间和良好的制备对映体纯的bis-1,3-dioxolanylmethyl硫属元素化物和二硫属元素化物。产量。此外，在与丙烯腈的迈克尔反应中评估了新的二硒化物4a，在两步之后得到（R）-3-[（2,3-二羟丙基）硒基]丙烷腈6b。