benzyl 6-deoxy-α-L-glucopyranoside | 220984-62-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 6-deoxy-α-L-glucopyranoside
• 英文别名: L-α-benzylquinovoside；(2S,3R,4R,5S,6R)-2-methyl-6-phenylmethoxyoxane-3,4,5-triol
• CAS: 220984-62-3
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: UHQDDNIUJBFOEL-AHRFKUBPSA-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-α-L-glucopyranoside 以 丙酮 为溶剂， 反应 48.0h， 以42%的产率得到benzyl 3-O-butanoyl-6-deoxy-α-L-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：

  2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl bromide 在 吡啶 、 lithium aluminium tetrahydride 、 sodium methylate 、 四氯化钛 、 mercury dibromide 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 benzyl 6-deoxy-α-L-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

• Selective Axial-to-Equatorial Epimerization of Carbohydrates
  作者：Hayden M. Carder、Yong Wang、Alison E. Wendlandt

  DOI：10.1021/jacs.2c04743

  日期：2022.7.6

  Radical-mediated transformations have emerged as powerful methods for the synthesis of rare and unnatural branched, deoxygenated, and isomeric sugars. Here, we describe a radical-mediated axial-to-equatorial alcohol epimerization method to transform abundant glycans into rare isomers. The method delivers highly predictable and selective reaction outcomes that are complementary to other sugar isomerization

  自由基介导的转化已成为合成稀有和非天然支链、脱氧和异构糖的有效方法。在这里，我们描述了一种自由基介导的轴向到赤道醇差向异构化方法，可将丰富的聚糖转化为稀有异构体。该方法提供高度可预测和选择性的反应结果，与其他糖异构化方法互补。异构体相互转化的合成效用通过方便的聚糖合成展示，包括一步糖多样化。机理研究表明，位点选择性和非对映选择性都是通过赤道位置的 α-羟基 C-H 键的高选择性 H 原子提取来实现的。