Z-3-O-Acetyl-2,4-O-benzylidene-1-O-tert-butyldimethylsilyl-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hex-5-enitol | 141240-13-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Z-3-O-Acetyl-2,4-O-benzylidene-1-O-tert-butyldimethylsilyl-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hex-5-enitol
• CAS: 141240-13-3
• 化学式: C₂₇H₃₄Cl₂O₅Si
• 分子量: 537.555
• InChiKey: QRCPXKKNZKGGHB-JBAKOVECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.44
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Z-3-O-Acetyl-2,4-O-benzylidene-1-O-tert-butyldimethylsilyl-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hex-5-enitol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以55.5%的产率得到Z-1-O-Acetyl-2,4-O-benzylidene-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hex-5-enitol
  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：

  (Z)-1,3-di-O-acetyl-2,4-O-benzylidene-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hex-5-enitol 在 吡啶 、 咪唑 、 sodium methylate 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.25h， 生成 Z-3-O-Acetyl-2,4-O-benzylidene-1-O-tert-butyldimethylsilyl-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hex-5-enitol
  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