2-O-(naphth-2-oxyacetyl)sucrose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-(naphth-2-oxyacetyl)sucrose
• 英文别名: [(2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2-naphthalen-2-yloxyacetate
• 化学式: C₂₄H₃₀O₁₃
• 分子量: 526.494
• InChiKey: VNPSYZOERIZTTO-VQXBOQCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  205
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  3-(naphth-2-oxyacetyl)thiazolidine-2-thione 、 蔗糖 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以49%的产率得到2-O-(naphth-2-oxyacetyl)sucrose
  参考文献：
  名称：

  New highly regioselective reactions of unprotected sucrose. Synthesis of 2-O-acylsucroses and 2-O-(N-alkylcarbamoyl)sucroses

  摘要：

  New methodologies which lead selectively to chosen regioisomeric mono-O-acylsucroses are described. The results indicate that a selective ionization of the free sugar makes the secondary 2-OH group of the glucose moiety more nucleophilic than the primary hydroxyls. New 2-O-acylsucroses 2 and 2-O-(N-alkylcarbamoyl)sucroses 3 were thus obtained in high yields.

  DOI：

  10.1021/jo00060a053

文献信息

• A new synthesis of 6-O-acylsucroses and of mixed 6,6′-di-O-acylsucroses
  作者：Krystyna Baczko、Caroline Nugier-Chauvin、Joseph Banoub、Pierre Thibault、Daniel Plusquellec

  DOI：10.1016/0008-6215(94)00341-c

  日期：1995.4

  unprotected sucrose in N,N-dimethylformamide and the appropriate 3-acylthiazolidine-2-thiones 6 or 3-acyl-5-methyl-1,3,4-thiadiazole-2(3H)-thiones 7. A selective ionization of the free sugar by sodium hydride or triethylamine, followed by acylation with 6, gave 2-O-acylsucroses which were subjected in situ to intramolecular isomerizations using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or an aqueous solution

  从N，N-二甲基甲酰胺中的未保护蔗糖和适当的3-酰基噻唑烷-2-硫酮6或3-酰基-5-甲基-1,3,4-噻二唑-2（ 3H）-硫酮7.用氢化钠或三乙胺选择性离子化游离糖，然后用6进行酰化，生成2-O-酰基蔗糖，然后使用1,8-二氮杂双环[5.4.0]对其进行分子内异构化。十一碳烯（DBU）或三乙胺的水溶液可产生6-O-酰基蔗糖。如果在DBU存在下将蔗糖用6或7酰化，则可以直接获得后者。而且，通过使用Mitsunobu反应很容易地从6'-单酰基化物获得混合的6,6'-二-O-酰基蔗糖，而没有伴随形成3'，4'-环氧化物。
• New highly regioselective reactions of unprotected sucrose. Synthesis of 2-O-acylsucroses and 2-O-(N-alkylcarbamoyl)sucroses
  作者：Caroline Chauvin、Krystyna Baczko、Daniel Plusquellec

  DOI：10.1021/jo00060a053

  日期：1993.4

  New methodologies which lead selectively to chosen regioisomeric mono-O-acylsucroses are described. The results indicate that a selective ionization of the free sugar makes the secondary 2-OH group of the glucose moiety more nucleophilic than the primary hydroxyls. New 2-O-acylsucroses 2 and 2-O-(N-alkylcarbamoyl)sucroses 3 were thus obtained in high yields.