S-tert-butyl <3(S*)-(methoxycarbonyl)-4(S*)-<3,4-(methylenedioxy)phenyl>-4-<(tert-butyldimethylsilyl)oxy>>butanethioate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: S-tert-butyl <3(S*)-(methoxycarbonyl)-4(S*)-<3,4-(methylenedioxy)phenyl>-4-<(tert-butyldimethylsilyl)oxy>>butanethioate
• 英文别名: methyl (2S)-2-[(S)-1,3-benzodioxol-5-yl-[tert-butyl(dimethyl)silyl]oxymethyl]-4-tert-butylsulfanyl-4-oxobutanoate
• 化学式: C₂₃H₃₆O₆SSi
• 分子量: 468.687
• InChiKey: SKSMKGFGEMCBJV-OXJNMPFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  S-tert-butyl <3(S*)-(methoxycarbonyl)-4(S*)-<3,4-(methylenedioxy)phenyl>-4-<(tert-butyldimethylsilyl)oxy>>butanethioate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以90%的产率得到
  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 tetrahydroborate 、 四丁基氟化铵 、 溶剂黄146 、 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 S-tert-butyl <3(S*)-(methoxycarbonyl)-4(S*)-<3,4-(methylenedioxy)phenyl>-4-<(tert-butyldimethylsilyl)oxy>>butanethioate
  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。
• First Stereocontrolled Syntheses of Unsymmetrically Substituted Bislactone Lignans:  Stereocontrolled Syntheses of Four Possible Isomers of Methyl 4,8-Dioxoxanthoxylol
  作者：Shin-ichi Yoshida、Tsuyoshi Ogiku、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1021/jo961733y

  日期：1997.3.1

  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.