1,6-anhydro-3-O-β-D-glucopyranosyl-β-D-glucopyranose | 137334-33-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,6-anhydro-3-O-β-D-glucopyranosyl-β-D-glucopyranose
• 英文别名: (2S,3R,4S,5S,6R)-2-[[(1R,2R,3S,4R,5R)-2,4-dihydroxy-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 137334-33-9
• 化学式: C₁₂H₂₀O₁₀
• 分子量: 324.285
• InChiKey: LMOPRRACIIJLBU-CSOAUFAESA-N

物化性质

• 沸点：
  664.1±55.0 °C(Predicted)
• 密度：
  1.74±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-3-O-β-D-glucopyranosyl-β-D-glucopyranose 生成 [(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[[(1R,2R,3S,4R,5R)-2,4-dibenzoyloxy-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy]oxan-2-yl]methyl benzoate
  参考文献：
  名称：

  Lorentzen, Jens Peter; Helpap, Barbara; Lockhoff, Oskar, Angewandte Chemie, 1991, vol. 103, # 12, p. 1731 - 1732

  摘要：

  DOI：
• 作为产物：
  描述：

  laminaribiose 在 2-氯-1,3-二甲基氯化咪唑啉 、 三乙胺 作用下， 以 water-d2 为溶剂， 反应 0.25h， 生成 1,6-anhydro-3-O-β-D-glucopyranosyl-β-D-glucopyranose
  参考文献：
  名称：

  Direct synthesis of 1,6-anhydro sugars from unprotected glycopyranoses by using 2-chloro-1,3-dimethylimidazolinium chloride

  摘要：

  Various 1,6-anhydro sugars have been synthesized directly from the corresponding unprotected glycopyranoses in excellent yields by using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as a dehydrative condensing agent. The reactions took place smoothly under mild reaction conditions in aqueous media. The present method would be a practical tool for synthesis of 1,6-anhydro derivatives of mono-saccharides, linear-oligosaccharides, and branched-oligosaccharides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.171

文献信息

• β-Selective <i>C</i>-Arylation of Diisobutylaluminum Hydride Modified 1,6-Anhydroglucose: Synthesis of Canagliflozin without Recourse to Conventional Protecting Groups
  作者：Julian P. Henschke、Chen-Wei Lin、Ping-Yu Wu、Wen-Shing Tsao、Jyh-Hsiung Liao、Pei-Chen Chiang

  DOI：10.1021/acs.joc.5b00601

  日期：2015.5.15

  'The beta-selective phenylation of benzyl and boronate protected 1,6-anhydroglucose and the direct phenylation of unprotected 1,6-anhydroglucose (10), pretreated with i-Bu2AlH, i-Bu3Al, Et3Al, Me3Al, or n-octyl(3)Al, with triphenylalane or aryl(chloro)alanes is reported. The utility of the unprotected version of the method is demonstrated by the synthesis of the SGLT2 inhibitor, canagliflozin (1a), from commercially available 10 in one C-C bond-forming step. This approach circumvents the need for conventional protecting groups, and therefore no formal protection and deprotection steps are required.

  报道了对苯甲基和硼酸酯保护的1,6-脱水葡萄糖的β选择性苯基化，以及对未保护的1,6-脱水葡萄糖（10），在用i-Bu2AlH、i-Bu3Al、Et3Al、Me3Al或n-octyl(3)Al预处理后，使用三苯基烷基或芳基(氯)烷基化试剂的直接苯基化。该方法的未保护版本的实用性通过从商业可得的10在一步C-C键形成步骤中合成SGLT2抑制剂卡格列净（1a）得到证明。该方法避免了传统保护基团的需要，因此不需要正式的保护和去保护步骤。