2(S*)-<α(S*)-<(tert-butyldimethylsilyl)oxy>-3,4-(methylenedioxy)benzyl>-3(S*)-carboxy-4(R*)-(3,4-dimethoxyphenyl)butyrolactone

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: 2(S*)-<α(S*)-<(tert-butyldimethylsilyl)oxy>-3,4-(methylenedioxy)benzyl>-3(S*)-carboxy-4(R*)-(3,4-dimethoxyphenyl)butyrolactone
• 英文别名: (2R,3S,4S)-4-[(S)-1,3-benzodioxol-5-yl-[tert-butyl(dimethyl)silyl]oxymethyl]-2-(3,4-dimethoxyphenyl)-5-oxooxolane-3-carboxylic acid
• 化学式: C₂₇H₃₄O₉Si
• 分子量: 530.647
• InChiKey: VXGJFPIQRHAJBT-NEWJYFPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2(S*)-<α(S*)-<(tert-butyldimethylsilyl)oxy>-3,4-(methylenedioxy)benzyl>-3(S*)-carboxy-4(R*)-(3,4-dimethoxyphenyl)butyrolactone 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (2R,3S,4S)-4-((S)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-2-(3,4-dimethoxy-phenyl)-5-oxo-tetrahydro-furan-3-carboxylic acid
  参考文献：
  名称：

  First Stereocontrolled Syntheses of Unsymmetrically Substituted Bislactone Lignans:  Stereocontrolled Syntheses of Four Possible Isomers of Methyl 4,8-Dioxoxanthoxylol

  摘要：

  An efficient method for stereocontrolled syntheses of the unsymmetrically substituted bislactone subgroup of the furofuran lignan has been developed based on a stereoselective aldol reaction of the acid anhydride 8 or 9 and an aromatic aldehyde employing methyl 4,8-dioxoxanthoxylol (1a), 4,8-dioxofargesin (1b), methyl 4,8-dioxopiperitol (2a) and their isomer 3a as the representative examples of the axial-equatorial 1, diequatorial 2, and diaxial 3 types of this series.

  DOI：

  10.1021/jo961733y
• 作为产物：
  描述：

  Benzo[1,3]dioxol-5-yl-(tert-butyl-dimethyl-silanyloxy)-acetonitrile 在 咪唑 、 sodium hydroxide 、 sodium tetrahydroborate 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 乙酸酐 、 双(三甲基硅烷基)氨基钾 、 溶剂黄146 、 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 27.83h， 生成 2(S*)-<α(S*)-<(tert-butyldimethylsilyl)oxy>-3,4-(methylenedioxy)benzyl>-3(S*)-carboxy-4(R*)-(3,4-dimethoxyphenyl)butyrolactone
  参考文献：
  名称：

  First Stereocontrolled Syntheses of Unsymmetrically Substituted Bislactone Lignans:  Stereocontrolled Syntheses of Four Possible Isomers of Methyl 4,8-Dioxoxanthoxylol

  摘要：

  An efficient method for stereocontrolled syntheses of the unsymmetrically substituted bislactone subgroup of the furofuran lignan has been developed based on a stereoselective aldol reaction of the acid anhydride 8 or 9 and an aromatic aldehyde employing methyl 4,8-dioxoxanthoxylol (1a), 4,8-dioxofargesin (1b), methyl 4,8-dioxopiperitol (2a) and their isomer 3a as the representative examples of the axial-equatorial 1, diequatorial 2, and diaxial 3 types of this series.

  DOI：

  10.1021/jo961733y

文献信息

• The first stereocontrolled synthesis of diequatorial bislactone furofuran lignans having two different aryl groups: A synthesis of methyl 4, 8-dioxopiperitol
  作者：Shin-ichi Yoshida、Tsuyoshi Ogiku、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1016/0040-4039(95)00080-v

  日期：1995.2

  Methyl 4, 8-dioxopiperitol (1), a representative example of the diequatorial bislactone furofuran lignans having two different aryl groups, was synthesized based on the stereocontrolled aldol reaction of the acid anhydride3 and veratral.

  基于酸酐3和芳族化合物的立体控制的羟醛反应，合成了甲基4、8-二氧戊哌醇（1），其为具有两个不同芳基的二水合双内酯呋喃呋喃木脂素的代表性实例。