(+)-<3(S),4(S),S(R)>-tert-butyl 3-(2-methoxyethoxymethoxy)-4-(tert-butyldimethylsiloxy)-5-(p-tolylsulfinyl)pentanoate | 163213-87-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-<3(S),4(S),S(R)>-tert-butyl 3-(2-methoxyethoxymethoxy)-4-(tert-butyldimethylsiloxy)-5-(p-tolylsulfinyl)pentanoate
• 英文别名: tert-butyl (3S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-3-(2-methoxyethoxymethoxy)-5-[(R)-(4-methylphenyl)sulfinyl]pentanoate
• CAS: 163213-87-4
• 化学式: C₂₆H₄₆O₇SSi
• 分子量: 530.799
• InChiKey: BAQCKFGTEPPDIF-DKMHWAAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  35
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  99.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (+)-<3(S),4(S),S(R)>-tert-butyl 3-(2-methoxyethoxymethoxy)-4-(tert-butyldimethylsiloxy)-5-(p-tolylsulfinyl)pentanoate 在 镍 作用下， 以 乙醇 为溶剂， 以92%的产率得到(-)-<3(S),4(R)>-tert-butyl 3-(2-methoxyethoxymethoxy)-4-(tert-butyldimethylsilyloxy)pentanoate
  参考文献：
  名称：

  Asymmetric synthesis induced by chiral sulfoxides : 2-deoxy-sugars from β-ketoesters via malic acid.

  摘要：

  the asymmetric synthesis of(S)-malic esters was carried out by reduction of beta-ketosulfoxides derived from beta-ketoesters as well as the transformation of(S)-malic esters into syn and anti-1,2-diols via the reduction of beta-keto-gamma-alkoxy-sulfoxides. An application to the preparation of 2-deoxy-D-ribose and 2-deoxy-L-xylose derivatives is described.

  DOI：

  10.1016/0957-4166(94)80083-9
• 作为产物：
  描述：

  (+)(R) tert-butyl 3-oxo-4-(p-tolylsulfinyl)butyrate 在 咪唑 、 重铬酸吡啶 、 sodium acetate 、 镍 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 zinc dibromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 110.67h， 生成 (+)-<3(S),4(S),S(R)>-tert-butyl 3-(2-methoxyethoxymethoxy)-4-(tert-butyldimethylsiloxy)-5-(p-tolylsulfinyl)pentanoate
  参考文献：
  名称：

  Asymmetric synthesis induced by chiral sulfoxides : 2-deoxy-sugars from β-ketoesters via malic acid.

  摘要：

  the asymmetric synthesis of(S)-malic esters was carried out by reduction of beta-ketosulfoxides derived from beta-ketoesters as well as the transformation of(S)-malic esters into syn and anti-1,2-diols via the reduction of beta-keto-gamma-alkoxy-sulfoxides. An application to the preparation of 2-deoxy-D-ribose and 2-deoxy-L-xylose derivatives is described.

  DOI：

  10.1016/0957-4166(94)80083-9

文献信息

• Asymmetric synthesis induced by chiral sulfoxides : 2-deoxy-sugars from β-ketoesters via malic acid.
  作者：Guy Solladié、Antonio Almario

  DOI：10.1016/0957-4166(94)80083-9

  日期：1994.9

  the asymmetric synthesis of(S)-malic esters was carried out by reduction of beta-ketosulfoxides derived from beta-ketoesters as well as the transformation of(S)-malic esters into syn and anti-1,2-diols via the reduction of beta-keto-gamma-alkoxy-sulfoxides. An application to the preparation of 2-deoxy-D-ribose and 2-deoxy-L-xylose derivatives is described.