1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (-)-(S)-propanesulfinate | 144712-62-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (-)-(S)-propanesulfinate
• 英文别名: 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl-(-)-(S)-propanesufinate；[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] (S)-propane-1-sulfinate
• CAS: 144712-62-9
• 化学式: C₁₅H₂₆O₇S
• 分子量: 350.433
• InChiKey: MUSOGBBXUBSLSY-SCVVSUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (-)-(S)-propanesulfinate 、 对甲苯基溴化镁 以 甲苯 为溶剂， 反应 1.0h， 以89%的产率得到(S)-1-(propylsulfinyl)-4-methylbenzene
  参考文献：
  名称：

  Asymmetric synthesis of alkane- and arenesulfinates of diacetone-D-glucose (DAG): an improved and general route to both enantiomerically pure sulfoxides

  摘要：

  Diacetone-D-glucose (DAG), a commercially available, sugar-derived secondary alcohol, was found to react with alkane- and arenesulfinyl chlorides in the presence of a tertiary amine in a very useful manner. When i-Pr2Net is used as the base, (-)-(S)-alkane- and arenesulfinates are obtained in 50-90% yield with 89-greater-than-or-equal-to 95% de. Simply changing the base from i-Pr2NEt to Py affords (+)-(R)-alkane- and arenesulfinates in 56-87% yield with 70-greater-than-or-equal-to 95% de. The de's were determined by H-1 NMR. Optically pure alkane- and arenesulfinates are obtained either by recrystallization or by column chromatography. These sulfinates were transformed into various enantiomerically pure sulfoxides (alkyl alkyl and alkyl aryl) by reaction with different Grignard reagents. This new methodology is cheap, quick, and very convenient when both enantiomers of a given sulfoxide are needed enantiomerically pure. The influence of the solvent, as well as the effect of other types of bases, on the stereochemical course of the reaction has been evaluated, and a possible origin of the diastereoselectivity is discussed. Other optically pure secondary alcohols are used m the same reaction, and the comparison of their behavior with that of DAG is also reported.

  DOI：

  10.1021/jo00051a022
• 作为产物：
  描述：

  propane-1-sulfinyl chloride 、 双丙酮葡萄糖 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 以84%的产率得到1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (-)-(S)-propanesulfinate
  参考文献：
  名称：

  Saenz; Garcia; Guerrero de la Rosa, Il Farmaco, 1996, vol. 51, # 8-9, p. 613 - 615

  摘要：

  DOI：

文献信息

• Alcudia, Felipe; Fernandez, Inmaculada; Khiar, Noureddine, Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 74, # 1-4, p. 393 - 394
  作者：Alcudia, Felipe、Fernandez, Inmaculada、Khiar, Noureddine、Llera, Jose Manuel

  DOI：——

  日期：——