2-naphthyl 6-O-acetyl-β-D-glucopyranoside | 220984-72-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-naphthyl 6-O-acetyl-β-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-naphthalen-2-yloxyoxan-2-yl]methyl acetate
• CAS: 220984-72-5
• 化学式: C₁₈H₂₀O₇
• 分子量: 348.353
• InChiKey: QZERWLRASXTYKN-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  正丁酸2,2,2-三氟乙酯 、 2-naphthyl 6-O-acetyl-β-D-glucopyranoside 在 subtilisin 作用下， 以 丙酮 为溶剂， 生成 naphthyl 3-O-butanoyl-6-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  On the regioselectivity of the protease subtilisin towards the acylation of enantiomeric pairs of benzyl and naphthyl glycopyranosides. Part 2

  摘要：

  Subtilisin-catalyzed esterification of several enantiomeric benzyl and naphthyl glycopyranosides has been investigated. The D-sugar derivatives were all good substrates and subtilisin regioselectivity was similar with all the compounds tested, the 3-OH being acylated predominantly. On the other hand, most of the L-glycopyranosides were transformed during longer reaction times with a lower regioselectivity, the 2-OH being preferentially but not exclusively acylated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01217-4
• 作为产物：
  描述：

  tributyltin 2-naphthoxide 在 3 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 4.0h， 生成 2-naphthyl 6-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  On the regioselectivity of the protease subtilisin towards the acylation of enantiomeric pairs of benzyl and naphthyl glycopyranosides. Part 2

  摘要：

  Subtilisin-catalyzed esterification of several enantiomeric benzyl and naphthyl glycopyranosides has been investigated. The D-sugar derivatives were all good substrates and subtilisin regioselectivity was similar with all the compounds tested, the 3-OH being acylated predominantly. On the other hand, most of the L-glycopyranosides were transformed during longer reaction times with a lower regioselectivity, the 2-OH being preferentially but not exclusively acylated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01217-4