1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (+)-(R)-ethanesulfinate | 144787-79-1

• 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 (+)-(R)-ethanesulfinate
• 英文别名: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (R)-ethanesulfinate；[(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] (R)-ethanesulfinate
• CAS: 144787-79-1
• 化学式: C₁₄H₂₄O₇S
• 分子量: 336.406
• InChiKey: GQJMLAYWPBXEBA-CYLSLRBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  91.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (甲硫基)甲基锂 、 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (+)-(R)-ethanesulfinate 以 四氢呋喃 为溶剂， 反应 2.0h， 以46%的产率得到(R)-ethyl methylsulfanylmethyl sulfoxide
  参考文献：
  名称：

  Enantioselective preparation of alkyl alkylsulfanylmethyl sulfoxides and 4,5-dihydroisoxazoles from alkanesulfinates of 1,2 : 5,6-di-O-isopropylidene-D-glucose

  摘要：

  Reaction of (R) and (S)-alkanesulfinates of 1,2:5,6-di-O-isopropylidene-D-glucose (DAG) with methylsulfanylmethyllithium produces their corresponding dithioacetal mono-S-oxides with enantiomeric excesses ranging from 95 to 100%. On the other hand, exo-metallation of 3-methyl-4,5-dihydroisoxazoles and their subsequent reaction with (R)- and (S)-alkanesulfinates of DAG produces optically active 3-ethylsulfinylmethyl-4,5-dihydroisoxazoles.

  DOI：

  10.1039/p19940002177
• 作为产物：
  描述：

  ethanesulfinyl chloride 、 双丙酮葡萄糖 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以94%的产率得到1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (+)-(R)-ethanesulfinate
  参考文献：
  名称：

  Enantioselective preparation of alkyl alkylsulfanylmethyl sulfoxides and 4,5-dihydroisoxazoles from alkanesulfinates of 1,2 : 5,6-di-O-isopropylidene-D-glucose

  摘要：

  Reaction of (R) and (S)-alkanesulfinates of 1,2:5,6-di-O-isopropylidene-D-glucose (DAG) with methylsulfanylmethyllithium produces their corresponding dithioacetal mono-S-oxides with enantiomeric excesses ranging from 95 to 100%. On the other hand, exo-metallation of 3-methyl-4,5-dihydroisoxazoles and their subsequent reaction with (R)- and (S)-alkanesulfinates of DAG produces optically active 3-ethylsulfinylmethyl-4,5-dihydroisoxazoles.

  DOI：

  10.1039/p19940002177

文献信息

• Asymmetric synthesis of alkane- and arenesulfinates of diacetone-D-glucose (DAG): an improved and general route to both enantiomerically pure sulfoxides
  作者：I. Fernandez、N. Khiar、J. M. Llera、F. Alcudia

  DOI：10.1021/jo00051a022

  日期：1992.12

  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.
• 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：——
• Enantioselective preparation of alkyl alkylsulfanylmethyl sulfoxides and 4,5-dihydroisoxazoles from alkanesulfinates of 1,2 : 5,6-di-O-isopropylidene-<scp>D</scp>-glucose
  作者：Yolanda Arroyo-Gómez、Juan A. López-Sastre、Justo F. Rodríguez-Amo、Mercedes Santos-García、María A. Sanz-Tejedor

  DOI：10.1039/p19940002177

  日期：——

  Reaction of (R) and (S)-alkanesulfinates of 1,2:5,6-di-O-isopropylidene-D-glucose (DAG) with methylsulfanylmethyllithium produces their corresponding dithioacetal mono-S-oxides with enantiomeric excesses ranging from 95 to 100%. On the other hand, exo-metallation of 3-methyl-4,5-dihydroisoxazoles and their subsequent reaction with (R)- and (S)-alkanesulfinates of DAG produces optically active 3-ethylsulfinylmethyl-4,5-dihydroisoxazoles.