3-O-methyl-6-n-toluolsulfonyl-1,2-O-cyclohexylidene-α-D-glucofuranose | 71069-25-5

• 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-O-methyl-6-n-toluolsulfonyl-1,2-O-cyclohexylidene-α-D-glucofuranose
• 英文别名: 1,2-O-cyclohexylidene-3-O-methyl-α-D-glucofuranose 6-tosylate；[(2R)-2-[(3aR,5R,6S,6aR)-6-methoxyspiro[3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-2,1'-cyclohexane]-5-yl]-2-hydroxyethyl] 4-methylbenzenesulfonate
• CAS: 71069-25-5
• 化学式: C₂₀H₂₈O₈S
• 分子量: 428.504
• InChiKey: BLXXKOSDSYPABB-UJWQCDCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-O-methyl-6-n-toluolsulfonyl-1,2-O-cyclohexylidene-α-D-glucofuranose 在 四丁基氯化铵 barium hydroxide octahydrate 作用下， 以 苯 为溶剂， 反应 1.0h， 以68%的产率得到1,2-O-cyclohexylidene-3-O-methyl-5,6-anhydro-α-L-glucofuranose
  参考文献：
  名称：

  Zhdanov, Yu. A.; Alekseev, Yu. E.; Alekseeva, V. G., Journal of general chemistry of the USSR, 1988, vol. 58, # 11, p. 2325 - 2329

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-O-cyclohexylidene-3-O-methyl-α-D-glucofuranose 、 对甲苯磺酰氯 在 苄基三丁基氯化铵 sodium carbonate 、 calcium carbonate 作用下， 以 苯 为溶剂， 反应 2.0h， 以58.6%的产率得到3-O-methyl-6-n-toluolsulfonyl-1,2-O-cyclohexylidene-α-D-glucofuranose
  参考文献：
  名称：

  Zhdanov, Yu. A.; Alekseev, Yu. E.; Alekseeva, V. G., Journal of general chemistry of the USSR, 1988, vol. 58, # 11, p. 2325 - 2329

  摘要：

  DOI：

文献信息

• Dibutyltin Oxide Catalyzed Selective Sulfonylation of α-Chelatable Primary Alcohols
  作者：Michael J. Martinelli、Naresh K. Nayyar、Eric D. Moher、Ulhas P. Dhokte、Joseph M. Pawlak、Rajappa Vaidyanathan

  DOI：10.1021/ol990658l

  日期：1999.8.1

  The reaction of substituted glycols with catalytic dibutyltin oxide, stoichiometric p-toluenesulfonyl chloride, and triethylamine in CH2Cl2 resulted in the complete and rapid sulfonylation at the primary alcohol, The alpha-heterosubstituted primary alcohol moiety appeared optimal for best results, supporting the intermediacy of a five-membered chelate, The role of the amine is discussed, in addition to catalyst requirements and solvent effects.
• ZHDANOV, YU. A.;ALEKSEEV, YU. E.;ALEKSEEVA, V. G.;POLENOV, V. A.;KOROL, E+, ZH. OBSHCH. XIMII, 58,(1988) N 11, S. 2612-2617
  作者：ZHDANOV, YU. A.、ALEKSEEV, YU. E.、ALEKSEEVA, V. G.、POLENOV, V. A.、KOROL, E+

  DOI：——

  日期：——
• Catalytic Regioselective Sulfonylation of α-Chelatable Alcohols:  Scope and Mechanistic Insight
  作者：Michael J. Martinelli、Rajappa Vaidyanathan、Joseph M. Pawlak、Naresh K. Nayyar、Ulhas P. Dhokte、Christopher W. Doecke、Lisa M. H. Zollars、Eric D. Moher、Vien Van Khau、Berta Košmrlj

  DOI：10.1021/ja016031r

  日期：2002.4.1

  This paper describes a convenient protocol for the regioselective sulfonylation of alpha-chelatable alcohols. Typically, the reaction of alpha-heterosubstituted alcohols with 1 equiv of p-TsCl and 1 equiv of Et3N in the presence of 2 mol % of Bu2SnO leads to rapid, regioselective, and exclusive monotosylation. The pKa of the amine was correlated to the reaction rate. A plausible mechanism for this reaction has been proposed on the basis of Sn-119 NMR studies.
• Zhdanov, Yu. A.; Alekseev, Yu. E.; Alekseeva, V. G., Journal of general chemistry of the USSR, 1988, vol. 58, # 11, p. 2325 - 2329
  作者：Zhdanov, Yu. A.、Alekseev, Yu. E.、Alekseeva, V. G.、Polenov, V. A.、Korol', E. L.、et al.

  DOI：——

  日期：——