(-)-(2S,3R)-5-(2,5-dimethoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidene-4-methylpentene | 130353-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (-)-(2S,3R)-5-(2,5-dimethoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidene-4-methylpentene
• 英文别名: (4S,5R)-4-[(2,5-dimethoxyphenyl)methyl]-5-ethenyl-2,2,4-trimethyl-1,3-dioxolane
• CAS: 130353-07-0
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: LVQNONQXTXHMCE-WBVHZDCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (-)-(2S,3R)-5-(2,5-dimethoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidene-4-methylpentene 在 sodium periodate 、 四氧化锇 作用下， 以 乙醚 、 水 为溶剂， 反应 48.0h， 以80%的产率得到(-)-(2S,3S)-4-(2,5-dimethoxyphenyl)-2,3-dihydroxy-2,3-O-isopropylidene-3-methylbutanal
  参考文献：
  名称：

  Anthracyclinones. 5. Glucosaccharino-1,4-lactone as a chiral template for the synthesis of new anthracyclinones

  摘要：

  Alkylation of dimethoxybenzene 16 with the chiral aldehyde derivative 14 prepared in six steps from alpha-D-glucosaccharino,1,4-lactone 3 afforded the adduct 17. After suitable transformation of 17, A ring closure was stereoselectively performed using SnCl4 at -70-degrees-C, giving 20. The tetralin-type quinone monoketal 23 obtained from 20 was then condensed with 27, and complete deprotection of anthracyclinones 28 and 29 led to 9-deacetyl-8(R)-hydroxy-9-methyl-4-demethoxydaunomycinone (6). On the other hand, 39, easily obtained from 14, was condensed with leucoquinizarin 31 to give after oxidation, intramolecular Marschalk reaction and benzylic deoxygenation, the corresponding 7-deoxyaglycon 7.

  DOI：

  10.1021/jo00001a073
• 作为产物：
  描述：

  2,3-O-Isopropyliden-2-C-methyl-5-O-p-toluolsulfonyl-D-ribo-pentonsaeure-γ-lacton 在 偶氮二异丁腈 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 三正丁基氢锡 、 溶剂黄146 、 甲基磺酰氯 、 三乙胺 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 、 水 、 甲苯 、 丁酮 为溶剂， 反应 36.0h， 生成 (-)-(2S,3R)-5-(2,5-dimethoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidene-4-methylpentene
  参考文献：
  名称：

  Anthracyclinones. 5. Glucosaccharino-1,4-lactone as a chiral template for the synthesis of new anthracyclinones

  摘要：

  Alkylation of dimethoxybenzene 16 with the chiral aldehyde derivative 14 prepared in six steps from alpha-D-glucosaccharino,1,4-lactone 3 afforded the adduct 17. After suitable transformation of 17, A ring closure was stereoselectively performed using SnCl4 at -70-degrees-C, giving 20. The tetralin-type quinone monoketal 23 obtained from 20 was then condensed with 27, and complete deprotection of anthracyclinones 28 and 29 led to 9-deacetyl-8(R)-hydroxy-9-methyl-4-demethoxydaunomycinone (6). On the other hand, 39, easily obtained from 14, was condensed with leucoquinizarin 31 to give after oxidation, intramolecular Marschalk reaction and benzylic deoxygenation, the corresponding 7-deoxyaglycon 7.

  DOI：

  10.1021/jo00001a073

文献信息

• DEGUIN, BRIGITTE;FLORENT, JEAN-CLAUDE;MONNERET, CLAUDE, J. ORG. CHEM., 56,(1991) N, C. 405-411
  作者：DEGUIN, BRIGITTE、FLORENT, JEAN-CLAUDE、MONNERET, CLAUDE

  DOI：——

  日期：——