(1R,2R,3S)-<(tert-butyldimethylsilyl)oxy>-1,2,3,4,5,8-hexahydro-1,2,3-trihydroxy-2,3-O-isopropylidene-2-methyl-8,8-dimethoxy-5-oxonaphthalene | 130353-21-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,3S)-<(tert-butyldimethylsilyl)oxy>-1,2,3,4,5,8-hexahydro-1,2,3-trihydroxy-2,3-O-isopropylidene-2-methyl-8,8-dimethoxy-5-oxonaphthalene
• 英文别名: (3aR,4R,9aS)-4-[tert-butyl(dimethyl)silyl]oxy-5,5-dimethoxy-2,2,9a-trimethyl-4,9-dihydro-3aH-benzo[f][1,3]benzodioxol-8-one
• CAS: 130353-21-8
• 化学式: C₂₂H₃₆O₆Si
• 分子量: 424.61
• InChiKey: UKSAVTMZOHJOCS-OPYAIIAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S)-<(tert-butyldimethylsilyl)oxy>-1,2,3,4,5,8-hexahydro-1,2,3-trihydroxy-2,3-O-isopropylidene-3-methyl-5,5-dimethoxy-8-oxonaphthalene 、 (1R,2R,3S)-<(tert-butyldimethylsilyl)oxy>-1,2,3,4,5,8-hexahydro-1,2,3-trihydroxy-2,3-O-isopropylidene-2-methyl-8,8-dimethoxy-5-oxonaphthalene 、 3-氰苯酞 生成 (7R,8R,9S)-7-<(tert-butyldimethylsilyl)oxy>-7,8,9,10-tetrahydro-6,7,8,9-tetrahydroxy-8,9-O-isopropylidene-11-methoxy-9-methyl-5,12-naphthalenequinone
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  (+)-(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 生成 (1R,2R,3S)-<(tert-butyldimethylsilyl)oxy>-1,2,3,4,5,8-hexahydro-1,2,3-trihydroxy-2,3-O-isopropylidene-2-methyl-8,8-dimethoxy-5-oxonaphthalene
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• 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.