Bis<2,3,4-Tri-O-acetyl-1,5,6-trideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hexytol> 1,1'-disulfide | 141240-45-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: Bis<2,3,4-Tri-O-acetyl-1,5,6-trideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hexytol> 1,1'-disulfide
• CAS: 141240-45-1
• 化学式: C₃₆H₄₂Cl₄O₁₂S₂
• 分子量: 872.666
• InChiKey: VWTMYZSAGWATNU-XYTQFZDWSA-N

物化性质

• 沸点：
  768.1±60.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.84
• 重原子数：
  54.0
• 可旋转键数：
  21.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  157.8
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  Bis<2,3,4-Tri-O-acetyl-1,5,6-trideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hexytol> 1,1'-disulfide 在 potassium permanganate 、 sodium methylate 作用下， 生成 Sodium 6-(2,4-dichlorophenyl)-D-xylo-2,3,4-trihydroxyhexanesulfonate
  参考文献：
  名称：

  Synthesis of 2,6,7-trideoxy-7-C-(2,4-dichlorophenyl)-d-xylo-heptonic acid and 6-(2,4-dichlorophenyl)-d-xylo-2,3,4-trihydroxyhexanesulfonic acid

  摘要：

  2,4-O-Benzylidene-L-xylose was converted via a Wittig reaction into Z-2,4-O-benzylidene-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hex-5-enitol (17), which, on hydrogenation, gave 5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hexitol (33). tert-Butyldimethylsililation of the primary hydroxyl group of 33, followed by 4-methoxybenzylation, and desilylation afforded 5,6-dideoxy-6-C-(2,4-dichlorophenyl)-2,3,4-tri-O-(4-methoxybenzyl)-D-xylo-hexitol (54). A Mitsunobu-type reaction of 54 replaced HO-1 by cyanide to give, after hydrolysis and hydrogenolysis, 2,6,7-trideoxy-7-C-(2,4-dichlorophenyl)-D-xylo-heptono-1,4-lactone (55). Mesylation of 33 and then acetylation gave 2,3,4-tri-O-acetyl-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-1-O-methanesulfonyl-D-xylo-hexitol (63), which was converted via its 1-thiobenzoate into bis[1,5,6-trideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hexitol] 1,1'-disulfide (65). Acetylation of 65, followed by permanganate oxidation and deacetylation, afforded sodium 6-(2,4-dichlorophenyl)-D-xylo-2,3,4-trihydroxy-hexanesulfonate (67). Both 57 (obtained from 55 by hydrolysis with NaOH) and 67 are weak inhibitors of HMG-CoA reductase.

  DOI：

  10.1016/s0008-6215(00)90499-3
• 作为产物：
  描述：

  乙酸酐 、 Bis<1,5,6-trideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hexytol> 1,1'-disulfide 在 吡啶 作用下， 反应 20.0h， 以89%的产率得到Bis<2,3,4-Tri-O-acetyl-1,5,6-trideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hexytol> 1,1'-disulfide
  参考文献：
  名称：

  Synthesis of 2,6,7-trideoxy-7-C-(2,4-dichlorophenyl)-d-xylo-heptonic acid and 6-(2,4-dichlorophenyl)-d-xylo-2,3,4-trihydroxyhexanesulfonic acid

  摘要：

  2,4-O-Benzylidene-L-xylose was converted via a Wittig reaction into Z-2,4-O-benzylidene-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hex-5-enitol (17), which, on hydrogenation, gave 5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hexitol (33). tert-Butyldimethylsililation of the primary hydroxyl group of 33, followed by 4-methoxybenzylation, and desilylation afforded 5,6-dideoxy-6-C-(2,4-dichlorophenyl)-2,3,4-tri-O-(4-methoxybenzyl)-D-xylo-hexitol (54). A Mitsunobu-type reaction of 54 replaced HO-1 by cyanide to give, after hydrolysis and hydrogenolysis, 2,6,7-trideoxy-7-C-(2,4-dichlorophenyl)-D-xylo-heptono-1,4-lactone (55). Mesylation of 33 and then acetylation gave 2,3,4-tri-O-acetyl-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-1-O-methanesulfonyl-D-xylo-hexitol (63), which was converted via its 1-thiobenzoate into bis[1,5,6-trideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hexitol] 1,1'-disulfide (65). Acetylation of 65, followed by permanganate oxidation and deacetylation, afforded sodium 6-(2,4-dichlorophenyl)-D-xylo-2,3,4-trihydroxy-hexanesulfonate (67). Both 57 (obtained from 55 by hydrolysis with NaOH) and 67 are weak inhibitors of HMG-CoA reductase.

  DOI：

  10.1016/s0008-6215(00)90499-3