methyl 3,6-di-O-(4-toluenesulfonyl)-α-D-galactopyranoside | 74042-86-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,6-di-O-(4-toluenesulfonyl)-α-D-galactopyranoside
• 英文别名: methyl-3,6-di-O-(4-toluenesulfonyl)-α-D-galactopyranoside；methyl 3,6-di-O-p-tolylsulfonyl-α-D-galactopyranoside；methyl 3,6-di-O-tosyl-α-D-galactopyranoside；Tos(-3)[Tos(-6)]a-Gal1Me；[(2R,3S,4S,5R,6S)-3,5-dihydroxy-6-methoxy-4-(4-methylphenyl)sulfonyloxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 74042-86-7
• 化学式: C₂₁H₂₆O₁₀S₂
• 分子量: 502.563
• InChiKey: KVHBPUHVQBSCNL-TXVWBRJLSA-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：

  methyl β-D-galactopyranoside 生成 methyl 3,6-di-O-(4-toluenesulfonyl)-α-D-galactopyranoside
  参考文献：
  名称：

  KONDO, YOTARO, AGR. AND BIOL. CHEM., 52,(1988) N 5, 1313-1315

  摘要：

  DOI：

文献信息

• Chiral Benzazaborole‐Catalyzed Regioselective Sulfonylation of Unprotected Carbohydrate Derivatives
  作者：Satoru Kuwano、Yusei Hosaka、Takayoshi Arai

  DOI：10.1002/chem.201903443

  日期：2019.10.8

  Chiral benzazaborole-catalyzed regioselective sulfonylations of unprotected carbohydrate derivatives have been developed. This methodology enables direct regioselective functionalization of the secondary OH group in carbohydrate in the presence of the primary OH group. By using the chiral organoboron catalysis, kinetic resolution of the carbohydrate derivatives was also achieved.

  已经开发了未保护的碳水化合物衍生物的手性苯并氮杂硼烷催化的区域选择性磺酰化。该方法使得在存在伯OH基的情况下，能够直接对碳水化合物中的仲OH基进行区域选择性官能化。通过使用手性有机硼催化，还实现了碳水化合物衍生物的动力学拆分。
• Regioselective Sulfonylation/Acylation of Carbohydrates Catalyzed by FeCl₃ Combined with Benzoyltrifluoroacetone and Its Mechanism Study
  作者：Jian Lv、Jia-Jia Zhu、Yu Liu、Hai Dong

  DOI：10.1021/acs.joc.9b03128

  日期：2020.3.6

  A catalytic amount of FeCl3 combined with benzoyl trifluoroacetone (Hbtfa) (FeCl3/Hbtfa = 1/2) was used to catalyze sulfonylation/acylation of diols and polyols using diisopropylethylamine (DIPEA) or potassium carbonate (K2CO3) as a base. The catalytic system exhibited high catalytic activity, leading to excellent isolated yields of sulfonylation/acylation products with high regioselectivities. Mechanism

  使用二异丙基乙胺（DIPEA）或碳酸钾（K2CO3）作为碱，将催化量的FeCl3与苯甲酰基三氟丙酮（Hbtfa）（FeCl3 / Hbtfa = 1/2）结合用于催化二醇和多元醇的磺酰化/酰化。该催化体系表现出高催化活性，导致具有高区域选择性的磺酰化/酰化产物的优异分离产率。机理研究表明，FeCl3最初在碱性条件下于室温下于溶剂乙腈中以两倍的Hbtfa量形成[Fe（btfa）3]（btfa =苯甲酰基三氟丙酮酸酯）。然后，在碱的存在下，Fe（btfa）3和底物的两个羟基形成五元或六元环中间体。环状中间体和磺酰化试剂之间的随后反应导致底物的选择性磺酰化。所有关键中间体均在高分辨率质谱分析中捕获，因此首次证明了这种机理。
• Kondo, Yotaro, Agricultural and Biological Chemistry, 1988, vol. 52, # 5, p. 1313 - 1316
  作者：Kondo, Yotaro

  DOI：——

  日期：——
• 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.
• Selective p-toluenesulfonylation of methyl α-d-galactopyranoside
  作者：Betty Matsuhiro、Alberto B. Zanlungo

  DOI：10.1016/s0008-6215(00)85664-5

  日期：1980.5