(+)-(1R,2R,3S)-1,2,3-trihydroxy-1,2,3,4-tetrahydro-2,3-O-isopropylidene-3-methyl-5,8-dimethoxynaphthalene | 130353-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (+)-(1R,2R,3S)-1,2,3-trihydroxy-1,2,3,4-tetrahydro-2,3-O-isopropylidene-3-methyl-5,8-dimethoxynaphthalene
• 英文别名: (3aR,4R,9aS)-5,8-dimethoxy-2,2,9a-trimethyl-4,9-dihydro-3aH-benzo[f][1,3]benzodioxol-4-ol
• CAS: 130353-18-3
• 化学式: C₁₆H₂₂O₅
• 分子量: 294.348
• InChiKey: GSEGMBTXPVCXRY-FMKPAKJESA-N

物化性质

• 熔点：
  120 °C(Solvent: Hexane)
• 沸点：
  436.2±45.0 °C(predicted)
• 密度：
  1.173±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+)-(1R,2R,3S)-1,2,3-trihydroxy-1,2,3,4-tetrahydro-2,3-O-isopropylidene-3-methyl-5,8-dimethoxynaphthalene 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以96.5%的产率得到(+)-(1R,2R,3S)-1-<(tert-butyldimethylsilyl)oxy>-1,2,3,4-tetrahydro-1,2,3-trihydroxy-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：

  对苯二甲醚 在 偶氮二异丁腈 sodium periodate 、 四氧化锇 、 正丁基锂 、 三正丁基氢锡 、 四氯化锡 作用下， 以 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

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.