methyl 2,6-di-O-tosyl-α-D-mannopyranoside | 108825-74-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,6-di-O-tosyl-α-D-mannopyranoside
• 英文别名: Tos(-2)[Tos(-6)]a-Man1Me；[(2R,3S,4S,5S,6S)-3,4-dihydroxy-6-methoxy-5-(4-methylphenyl)sulfonyloxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 108825-74-7
• 化学式: C₂₁H₂₆O₁₀S₂
• 分子量: 502.563
• InChiKey: LETWHQSOZHSWKU-MJCUULBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  162
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  对甲苯磺酰氯 、 甲基-D-丙噻 在 二丁基二氯化锡 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以80%的产率得到methyl 3,6-di-O-tosyl-α-D-mannopyranoside
  参考文献：
  名称：

  One-Potp-Toluenesulfonylation of Adenosine and Methyl Glycosides with a Substoichiometric Amount of Organotin Mediators

  摘要：

  A substoichiometric amount (10-20 mol%) of dibutyltin dichloride 1 was found to be effective for promoting the regioselective 2'-O-tosylation of adenosine 2 with TsCl in a one-pot manner, wherein a turnover step for tin dichloride 1 was involved. Dibutylchlorotin hydroxide 7, dibutyltin oxide 8, bis(dibutylchlorotin) oxide 10, its hydroxy congener 12, and tributyltin chloride 14 were also effective ina substoichiometric amount for the 2'-O-tosylation of the nucleoside 2. The method was applicable to some methyl glycopyranosides, The tosylation with tin dichloride 1 was not sensitive to the presence of water in the reaction mixture. Possible reaction pathways are discussed.

  DOI：

  10.1080/07328300008544065

文献信息

• Partial tosylation of methyl α-d-mannopyranoside
  作者：Yôtaro Kondo

  DOI：10.1016/s0008-6215(00)90046-6

  日期：1986.10
• One-Pot<i>p</i>-Toluenesulfonylation of Adenosine and Methyl Glycosides with a Substoichiometric Amount of Organotin Mediators
  作者：Masajiro Kawana、Masafumi Tsujimoto、Shunya Takahashi

  DOI：10.1080/07328300008544065

  日期：2000.1

  A substoichiometric amount (10-20 mol%) of dibutyltin dichloride 1 was found to be effective for promoting the regioselective 2'-O-tosylation of adenosine 2 with TsCl in a one-pot manner, wherein a turnover step for tin dichloride 1 was involved. Dibutylchlorotin hydroxide 7, dibutyltin oxide 8, bis(dibutylchlorotin) oxide 10, its hydroxy congener 12, and tributyltin chloride 14 were also effective ina substoichiometric amount for the 2'-O-tosylation of the nucleoside 2. The method was applicable to some methyl glycopyranosides, The tosylation with tin dichloride 1 was not sensitive to the presence of water in the reaction mixture. Possible reaction pathways are discussed.