2-naphthyl α-L-rhamnopyranoside | 18918-48-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-naphthyl α-L-rhamnopyranoside
• 英文别名: 2-naphthyl-α-L-rhamnoside；2-naphthyl 6-deoxy-α-L-galactopyranoside；(2S,3R,4R,5R,6S)-2-methyl-6-naphthalen-2-yloxyoxane-3,4,5-triol
• CAS: 18918-48-4
• 化学式: C₁₆H₁₈O₅
• 分子量: 290.316
• InChiKey: HFJUQSUBZOKELZ-FSDJSFAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-naphthyl α-L-rhamnopyranoside 、 正丁酸2,2,2-三氟乙酯 在 subtilisin 作用下， 以 丙酮 为溶剂， 生成 Butyric acid (2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-2-(naphthalen-2-yloxy)-tetrahydro-pyran-3-yl ester 、 Butyric acid (2S,3S,4R,5R,6S)-3,5-dihydroxy-2-methyl-6-(naphthalen-2-yloxy)-tetrahydro-pyran-4-yl ester 、 Butyric acid (2S,3R,4S,5R,6S)-4,5-dihydroxy-2-methyl-6-(naphthalen-2-yloxy)-tetrahydro-pyran-3-yl ester
  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：

  L-rhamnopyranose 在 吡啶 、 3 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 生成 2-naphthyl α-L-rhamnopyranoside
  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

文献信息

• Synthesis of aryl α-<i>O-</i>L-rhamnopyranoside by two-step reaction in one pot
  作者：Nianping Liu、Xiangguang Tian、Zekun Ding、Yongda Zhou、Wan Zhang、Qingbing Wang、Yi Zhang、Yijun Gu、Jianbo Zhang

  DOI：10.1080/07328303.2017.1390578

  日期：2017.6.13

  approach in two steps and one pot using the rhamnopyranosyl chloride as key intermediate. The two-step one-pot procedure is more convenient and environmentally friendly, compared to the published synthetic routes. Besides, the structure-reactivity relationship and the plausible mechanism for this base-catalyzed glycosylation were discussed by means of the Hammett equation.

  图形摘要摘要使用鼠李糖吡喃糖基氯为主要中间体，通过两步一锅的相转移催化方法方便地合成了标题化合物。与公开的合成路线相比，两步一锅法更方便，更环保。此外，利用Hammett方程讨论了该碱催化的糖基化反应的结构-反应关系和合理的机理。
• On the regioselectivity of the protease subtilisin towards the acylation of enantiomeric pairs of benzyl and naphthyl glycopyranosides. Part 2
  作者：Bruno Danieli、Francesco Peri、Gabriella Roda、Giacomo Carrea、Sergio Riva

  DOI：10.1016/s0040-4020(98)01217-4

  日期：1999.2

  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.