(-)-(2R,3R)-methyl 2,3-dihydroxy-2,3-O-isopropylidene-2-methylpent-4-enoate | 85963-85-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(2R,3R)-methyl 2,3-dihydroxy-2,3-O-isopropylidene-2-methylpent-4-enoate
• 英文别名: (4R,5R)-2,2,4-Trimethyl-5-vinyl-1,3-dioxolan-4-carbonsaeure-methylester；Methyl (2R,3R)-2,3-dihydroxy-2,3-O-isopropylidene-2-methyl-4-pentenoate；methyl (4R,5R)-5-ethenyl-2,2,4-trimethyl-1,3-dioxolane-4-carboxylate
• CAS: 85963-85-5
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: KWZXVZCVLIOFDT-GMSGAONNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(2R,3R)-methyl 2,3-dihydroxy-2,3-O-isopropylidene-2-methylpent-4-enoate 在 偶氮二异丁腈 sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 正丁基锂 、 三正丁基氢锡 、 四氯化锡 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 77.5h， 生成 (+)-(1R,2R,3S)-1,2,3-trihydroxy-1,2,3,4-tetrahydro-2,3-O-isopropylidene-3-methyl-5,8-dimethoxynaphthalene
  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-异丙亚基-2-C-甲基-D-核糖酸-gamma-内酯 在 吡啶 、 Ni-Raney 、 sodium methylate 、 硫脲 作用下， 以 甲醇 为溶剂， 反应 42.0h， 生成 (-)-(2R,3R)-methyl 2,3-dihydroxy-2,3-O-isopropylidene-2-methylpent-4-enoate
  参考文献：
  名称：

  Lopez-Herrera, F. J.; Sarabia-Garcia, F.; Pino-Gonzalez, M. S., Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 767 - 776

  摘要：

  DOI：

文献信息

• Hoffmann, Reinhard W.; Ladner, Wolfgang, Chemische Berichte, 1983, vol. 116, # 4, p. 1631 - 1642
  作者：Hoffmann, Reinhard W.、Ladner, Wolfgang

  DOI：——

  日期：——
• 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：——
• Lopez-Herrera, F. J.; Sarabia-Garcia, F.; Pino-Gonzalez, M. S., Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 767 - 776
  作者：Lopez-Herrera, F. J.、Sarabia-Garcia, F.、Pino-Gonzalez, M. S.、Garcia-Aranda, J. F.

  DOI：——

  日期：——
• Anthracyclinones. 5. Glucosaccharino-1,4-lactone as a chiral template for the synthesis of new anthracyclinones
  作者：Brigitte Deguin、Jean Claude Florent、Claude Monneret

  DOI：10.1021/jo00001a073

  日期：1991.1

  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.