benzyl α-L-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl α-L-glucopyranoside
• 英文别名: benzyl-O-β-D-glucopyranoside；(2S,3R,4R,5S,6R)-2-(hydroxymethyl)-6-phenylmethoxyoxane-3,4,5-triol
• 化学式: C₁₃H₁₈O₆
• 分子量: 270.282
• InChiKey: GKHCBYYBLTXYEV-IEECTRCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl α-L-glucopyranoside 在 1-羟基苯并三唑 、 三乙胺 、 zinc(II) chloride 作用下， 反应 28.5h， 生成 benzyl 2-O-benzoyl-4,6-O-benzylidene-α-L-glucopyranoside
  参考文献：
  名称：

  分子内糖基化过程中的双重不对称诱导

  摘要：

  N-碘代琥珀酰亚胺激活由苯基 2,3,4-tri-O-benzyl-1-thio-α-L- 和 -D-mannopyranosides 构建的预先安排的糖苷，这些糖苷通过琥珀酰间隔物通过位置 6 连接到位置 3苄基 2-O-苯甲酰基-6-O-苄基-α-L-和-D-吡喃葡萄糖苷（6,3-预先排列的 L-Man/L-Glc、D-Man/D-Glc、L-Man/D -Glc 和 D-Man/L-Glc) 以 70-78% 的产率提供相应的 3,6'-琥珀酰桥连二糖 Man-(1→4)-Glc 的 α/β-混合物。分子内糖基化的非对映选择性与预先排列的糖苷的形貌特性无关（α-端基异构体在 L-Man/L-Glc 和 D-Man/D-Glc 中占主导地位），但取决于几何特性（β-端基异构体以 L-Man/D-Glc 和 D-Man/L-Glc 为主）。因此，在预先安排的糖苷的分子内糖基化过程中，双重不对称诱导是有效的。

  DOI：

  10.1002/(sici)1099-0690(199801)1998:1<163::aid-ejoc163>3.0.co;2-i
• 作为产物：
  描述：

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

• Synthesis of Benzyl Tetra-O-acetyl-α-L-glucopyranoside from Benzyl 2,3-Dideoxy-β-D-erythro-hex-2-enopyranoside
  作者：Takeshi Sugai、Hayato Okazaki、Yuji Ueda、Kengo Hanaya、Mitsuru Shoji

  DOI：10.3987/com-16-s(s)54

  日期：——

  Benzyl tetra-O-acetyl-alpha-L-glucopyranoside was synthesized from benzyl 2,3-dideoxy-beta-D-erythro-hex-2-enopyranoside in six steps and 19% overall yield. Epoxidation from the beta-side of the double bond between C-2 and C-3 of the starting material along with the subsequent regioselective ring opening by the backside attack of a hydroxide ion at C-3 furnished an intermediate with D-ido-stereochemistry. The inversion at C-5 was performed by an epimerization, by way of an N-cyclohexylenamine, after the chemoselective oxidation at primary hydroxy group of the C-6 to an aldehyde. The present synthesis of L-glucose derivatives implies the sequential stereochemical inversion of C-2 to C-5 of D-glucose. As the present synthesis keeps the whole skeleton and the order of carbon atoms based on the original numbering of D-glucose, it would work well for the synthesis of specifically labeled derivatives, beginning from isotopically labeled D-glucoses.
• 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.
• Double Asymmetric Induction During Intramolecular Glycosylation
  作者：Thomas Ziegler、Gregor Lemanski

  DOI：10.1002/(sici)1099-0690(199801)1998:1<163::aid-ejoc163>3.0.co;2-i

  日期：1998.1

  The diastereoselectivity of the intramolecular glycosylation is independent of the topographic properties of the prearranged glycosides (the α-anomers predominate for L-Man/L-Glc and D-Man/D-Glc) but depends on the geometric properties (the β-anomers predominate for L-Man/D-Glc and D-Man/L-Glc). Thus, a double asymmetric induction is operative during intramolecular glycosylation of prearranged glycosides

  N-碘代琥珀酰亚胺激活由苯基 2,3,4-tri-O-benzyl-1-thio-α-L- 和 -D-mannopyranosides 构建的预先安排的糖苷，这些糖苷通过琥珀酰间隔物通过位置 6 连接到位置 3苄基 2-O-苯甲酰基-6-O-苄基-α-L-和-D-吡喃葡萄糖苷（6,3-预先排列的 L-Man/L-Glc、D-Man/D-Glc、L-Man/D -Glc 和 D-Man/L-Glc) 以 70-78% 的产率提供相应的 3,6'-琥珀酰桥连二糖 Man-(1→4)-Glc 的 α/β-混合物。分子内糖基化的非对映选择性与预先排列的糖苷的形貌特性无关（α-端基异构体在 L-Man/L-Glc 和 D-Man/D-Glc 中占主导地位），但取决于几何特性（β-端基异构体以 L-Man/D-Glc 和 D-Man/L-Glc 为主）。因此，在预先安排的糖苷的分子内糖基化过程中，双重不对称诱导是有效的。