Methanesulfonic acid (1R,2R,3R,4R)-4-methanesulfonyloxy-2,3,5-tris-methoxymethoxy-1-methoxymethoxymethyl-pentyl ester | 219562-27-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Methanesulfonic acid (1R,2R,3R,4R)-4-methanesulfonyloxy-2,3,5-tris-methoxymethoxy-1-methoxymethoxymethyl-pentyl ester
• 英文别名: [(2R,3R,4R,5R)-1,3,4,6-tetrakis(methoxymethoxy)-5-methylsulfonyloxyhexan-2-yl] methanesulfonate
• CAS: 219562-27-3
• 化学式: C₁₆H₃₄O₁₄S₂
• 分子量: 514.57
• InChiKey: NETNRZLBKSSSDK-WCVJEAGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  32
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  177
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (1R,2R,3R,4R)-4-methanesulfonyloxy-2,3,5-tris-methoxymethoxy-1-methoxymethoxymethyl-pentyl ester 在 palladium dihydroxide 氢气 、 三氟乙酸 作用下， 以 溶剂黄146 为溶剂， 25.0~120.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 生成 2,5-dideoxy-2,5-imino-L-mannitol
  参考文献：
  名称：

  Enantioselective Approach to Polyhydroxylated Compounds Using Chiral Sulfoxides:  Synthesis of Enantiomerically Pure myo-Inositol and Pyrrolidine Derivatives

  摘要：

  A short enantioselective synthesis of the biologically important myo-inositol derivative I and the pyrrolidine derivative II is described. The molecule 3, a diketo disulfoxide readily made from tartaric acid, is the key intermediate. The sulfinyl group controlled completely the very high stereoselection observed.

  DOI：

  10.1021/jo9811569
• 作为产物：
  描述：

  (2R)-2-[(4S,5S)-5-[(1R)-2-hydroxy-1-phenylmethoxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylmethoxyethanol 在 palladium dihydroxide Dowex 50W-X₈ 、 氢气 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 22.5h， 生成 Methanesulfonic acid (1R,2R,3R,4R)-4-methanesulfonyloxy-2,3,5-tris-methoxymethoxy-1-methoxymethoxymethyl-pentyl ester
  参考文献：
  名称：

  Enantioselective Approach to Polyhydroxylated Compounds Using Chiral Sulfoxides:  Synthesis of Enantiomerically Pure myo-Inositol and Pyrrolidine Derivatives

  摘要：

  A short enantioselective synthesis of the biologically important myo-inositol derivative I and the pyrrolidine derivative II is described. The molecule 3, a diketo disulfoxide readily made from tartaric acid, is the key intermediate. The sulfinyl group controlled completely the very high stereoselection observed.

  DOI：

  10.1021/jo9811569

文献信息

• Enantioselective Approach to Polyhydroxylated Compounds Using Chiral Sulfoxides:  Synthesis of Enantiomerically Pure <i>myo</i>-Inositol and Pyrrolidine Derivatives
  作者：Françoise Colobert、Amélia Tito、Noureddine Khiar、Donatienne Denni、Maria Angeles Medina、Manuel Martin-Lomas、José-Luis Garcia Ruano、Guy Solladié

  DOI：10.1021/jo9811569

  日期：1998.11.1

  A short enantioselective synthesis of the biologically important myo-inositol derivative I and the pyrrolidine derivative II is described. The molecule 3, a diketo disulfoxide readily made from tartaric acid, is the key intermediate. The sulfinyl group controlled completely the very high stereoselection observed.