O³-Methyl-1,6-anhydro-β-D-glucopyranose | 35405-73-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: O³-Methyl-1,6-anhydro-β-D-glucopyranose
• 英文别名: 1,6-anhydro-3-O-methyl-β-D-glucopyranose；1,6-Anhydro-3-O-methyl-β-D-glucopyranose；1,6-anhydro-3-O-methyl-beta-d-glucopyranose；(1R,2R,3S,4R,5R)-3-methoxy-6,8-dioxabicyclo[3.2.1]octane-2,4-diol
• CAS: 35405-73-3
• 化学式: C₇H₁₂O₅
• 分子量: 176.169
• InChiKey: ULALVUIGQKRQHV-BNWJMWRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O³-Methyl-1,6-anhydro-β-D-glucopyranose 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 4-(dimethylamino)pyridine hydrochloride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 3-O-methyl-2,4-bis(3,4-(diphenylmethylenedioxy)-5-hydroxybenzoyl)-1,6-anhydro-β-D-glucopyranose
  参考文献：
  名称：

  Feldman, Ken S.; Iyer, Malliga R.; Liu, Yanze, Journal of Organic Chemistry, 2003, vol. 68, # 19, p. 7433 - 7438

  摘要：

  DOI：
• 作为产物：
  描述：

  3-O-methyl-D-glucopyranose 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 O³-Methyl-1,6-anhydro-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

• [EN] GLYCOSAMINOGLYCAN (GAG) MIMETICS<br/>[FR] COMPOSES MIMETIQUES DU GLYCOSAMINOGLYCANE (GAG)
  申请人：PROGEN IND LTD

  公开号：WO2005061523A1

  公开（公告）日：2005-07-07

  The invention relates to compounds that are designed to mimic the structure of GAGs; methods for the preparation of the compounds; compositions comprising the compounds; and use of the compounds and compositions thereof for the anti-angiogenic, anti-metastatic, anti-inflammatory, anticoagulant, antithrombotic, and/or antimicrobial treatment of a mammalian subject.

  本发明涉及旨在模仿GAGs结构的化合物；制备这些化合物的方法；包含这些化合物的组合物；以及将这些化合物及其组合物用于哺乳动物主体的抗血管生成、抗转移、抗炎、抗凝血、抗血栓和/或抗微生物治疗的用途。
• Cuprammonium--Glycoside Complexes. V. The Conformation of the Pyranose Ring in Some D-Hexose&lt;1,5&gt;β&lt;1,6&gt;Anhydrides
  作者：Richard E. Reeves

  DOI：10.1021/ja01174a058

  日期：1949.6
• Direct synthesis of 1,6-anhydro sugars from unprotected glycopyranoses by using 2-chloro-1,3-dimethylimidazolinium chloride
  作者：Tomonari Tanaka、Wei Chun Huang、Masato Noguchi、Atsushi Kobayashi、Shin-ichiro Shoda

  DOI：10.1016/j.tetlet.2009.02.171

  日期：2009.5

  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.
• Feldman, Ken S.; Iyer, Malliga R.; Liu, Yanze, Journal of Organic Chemistry, 2003, vol. 68, # 19, p. 7433 - 7438
  作者：Feldman, Ken S.、Iyer, Malliga R.、Liu, Yanze

  DOI：——

  日期：——