(3aR,4R,6R,6aR)-6-[2,2-bis(phenylsulfanyl)ethyl]-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole | 642408-86-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (3aR,4R,6R,6aR)-6-[2,2-bis(phenylsulfanyl)ethyl]-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS: 642408-86-4
• 化学式: C₂₂H₂₆O₄S₂
• 分子量: 418.578
• InChiKey: YMWWRYJHJLLYAR-CWJKEVGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  87.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,4R,6R,6aR)-6-[2,2-bis(phenylsulfanyl)ethyl]-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole 在 吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.33h， 生成 [(4R,5R)-5-[3-[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2,2-bis(phenylsulfanyl)propanoyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl acetate
  参考文献：
  名称：

  Addition of Lithiated C-Nucleophiles to 2,3-O-Isopropylidene-d-erythronolactone:  Stereoselective Formation of a Furanose C-Disaccharide

  摘要：

  Addition of PhLi and lithiated dithianes to 2,3-O-isopropylidene-D-erythronolactone affords lactols, which are reduced with Et3SiH to the corresponding C-glycosides, the structures of two of which have been solved by X-ray diffraction. The use of a D-ribose-derived lithiated dithiane nucleophile in this chemistry allows for the convenient construction of a furanose C-disaccharide.

  DOI：

  10.1021/jo0350256
• 作为产物：
  描述：

  甲基-2,3-O-异亚丙基-beta-D-呋喃核糖苷 在 吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.83h， 生成 (3aR,4R,6R,6aR)-6-[2,2-bis(phenylsulfanyl)ethyl]-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
  参考文献：
  名称：

  Addition of Lithiated C-Nucleophiles to 2,3-O-Isopropylidene-d-erythronolactone:  Stereoselective Formation of a Furanose C-Disaccharide

  摘要：

  Addition of PhLi and lithiated dithianes to 2,3-O-isopropylidene-D-erythronolactone affords lactols, which are reduced with Et3SiH to the corresponding C-glycosides, the structures of two of which have been solved by X-ray diffraction. The use of a D-ribose-derived lithiated dithiane nucleophile in this chemistry allows for the convenient construction of a furanose C-disaccharide.

  DOI：

  10.1021/jo0350256

文献信息

• Addition of Lithiated <i>C</i>-Nucleophiles to 2,3-<i>O</i>-Isopropylidene-<scp>d</scp>-erythronolactone:  Stereoselective Formation of a Furanose <i>C</i>-Disaccharide
  作者：Jason L. McCartney、Christopher T. Meta、Robert M. Cicchillo、Matthew D. Bernardina、Timothy R. Wagner、Peter Norris

  DOI：10.1021/jo0350256

  日期：2003.12.1

  Addition of PhLi and lithiated dithianes to 2,3-O-isopropylidene-D-erythronolactone affords lactols, which are reduced with Et3SiH to the corresponding C-glycosides, the structures of two of which have been solved by X-ray diffraction. The use of a D-ribose-derived lithiated dithiane nucleophile in this chemistry allows for the convenient construction of a furanose C-disaccharide.