(-)-(2R,3R)-2,3-dihydroxy-2,3-O-isopropylidene-2-methylpent-4-enal | 130353-13-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(2R,3R)-2,3-dihydroxy-2,3-O-isopropylidene-2-methylpent-4-enal
• 英文别名: (4R,5R)-5-ethenyl-2,2,4-trimethyl-1,3-dioxolane-4-carbaldehyde
• CAS: 130353-13-8
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: MSTORQMIQGDEDQ-APPZFPTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(2R,3R)-2,3-dihydroxy-2,3-O-isopropylidene-2-methylpent-4-enal 在 sodium periodate 、 四氧化锇 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成
  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：

  (-)-(2R,3R)-methyl 2,3-dihydroxy-2,3-O-isopropylidene-2-methylpent-4-enoate 在 lithium aluminium tetrahydride 、 重铬酸吡啶 、 3 A molecular sieve 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 0.75h， 生成 (-)-(2R,3R)-2,3-dihydroxy-2,3-O-isopropylidene-2-methylpent-4-enal
  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：——
• 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.