benzyl 6-deoxy-β-D-glucopyranoside | 220984-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 6-deoxy-β-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2-methyl-6-phenylmethoxyoxane-3,4,5-triol
• CAS: 220984-57-6
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: UHQDDNIUJBFOEL-KABOQKQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  正丁酸2,2,2-三氟乙酯 、 benzyl 6-deoxy-β-D-glucopyranoside 在 subtilisin 作用下， 以 丙酮 为溶剂， 生成 benzyl 3-O-butanoyl-6-deoxy-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：

  苄基 alpha-D-吡喃葡萄糖苷 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 benzyl 6-deoxy-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

文献信息

• 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.