phenyl-(tri-O-acetyl-α-D-arabino-2-deoxy-hexopyranoside) | 20196-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl-(tri-O-acetyl-α-D-arabino-2-deoxy-hexopyranoside)
• 英文别名: 1-O-phenyl-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside；3,4,6-tri-O-acetyl-2-deoxy-1-O-phenyl-α-D-mannopyranoside；phenyl-(tri-O-acetyl-α-D-arabino-2-deoxy-hexopyranoside)；Phenyl-(tri-O-acetyl-α-D-arabino-2-desoxy-hexopyranosid)；Phenyl-tri-O-acetyl-2-deoxy-α-D-arabino-hexopyranosid；Phenyl-2-desoxy-α-D-glucosid-triacetat
• CAS: 20196-78-5
• 化学式: C₁₈H₂₂O₈
• 分子量: 366.368
• InChiKey: ZLNOUVXLATXOGX-BDXSIMOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  phenyl-(tri-O-acetyl-α-D-arabino-2-deoxy-hexopyranoside) 在 甲醇 、 sodium methylate 作用下， 生成 phenyl 2-deoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  926. The preparation and properties of aryl 2-deozy-α-D-glucopyranosides

  摘要：

  DOI：

  10.1039/jr9570004612
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-S-acetyl-1-O-phenyl-α-D-mannopyranoside 在 一水合肼 、 tris(2,2'-bipyridyl)ruthenium dichloride 、 三(2-羰基乙基)磷盐酸盐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以83 %的产率得到phenyl-(tri-O-acetyl-α-D-arabino-2-deoxy-hexopyranoside)
  参考文献：
  名称：

  Visible-Light-Promoted Desulfurization to Synthesize Deoxyglycosides

  摘要：

  DOI：

  10.1021/acs.joc.3c00046

文献信息

• Copper-Catalyzed Anomeric O-Arylation of Carbohydrate Derivatives at Room Temperature
  作者：Tristan Verdelet、Sara Benmahdjoub、Belkacem Benmerad、Mouad Alami、Samir Messaoudi

  DOI：10.1021/acs.joc.9b01218

  日期：2019.7.19

  Direct and practical anomeric O-arylation of sugar lactols with substituted arylboronic acids has been established. Using copper catalysis at room temperature under an air atmosphere, the protocol proved to be general, and a variety of aryl O-glycosides have been prepared in good to excellent yields. Furthermore, this approach was extended successfully to unprotected carbohydrates, including α-mannose

  已经建立了糖乳醇与取代的芳基硼酸的直接和实用的异头O-芳基化。在室温，空气气氛下使用铜催化，证明该方案是通用的，并且已经以良好至优异的产率制备了各种芳基O-糖苷。此外，该方法已成功地扩展到未保护的碳水化合物（包括α-甘露糖），并在此证明了碳水化合物和硼酸之间的相互作用如何与铜催化结合以实现选择性的异头O-芳基化。
• Facile TMSOTf-catalyzed preparation of 2-deoxy α-O-aryl-D-glycosides from glycosyl acetates
  作者：Guofang Yang、Qingbing Wang、Xiaosheng Luo、Jianbo Zhang、Jie Tang

  DOI：10.1007/s10719-012-9429-7

  日期：2012.8

  2-Deoxy α-O-aryl glycosides were conveniently obtained by reaction of 2-deoxy-glycosyl acetates with phenols in the presence of TMSOTf as the promoter. The current method provides the O-aryl glycosides with good to excellent yields, and sole alpha selectivity.

  在以 TMSOTf 为促进剂的存在下，通过 2-脱氧-糖基乙酸酯与苯酚的反应，可以方便地获得 2-脱氧 α-O-芳基苷。目前的方法可以提供良好到极佳收率的 O-芳基苷，并具有唯一的α选择性。
• A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light To Synthesize Deoxyglycosides
  作者：Jian-Tao Ge、Lang Zhou、Tao Luo、Jian Lv、Hai Dong

  DOI：10.1021/acs.orglett.9b02033

  日期：2019.8.2

  We herein developed an efficient method for removing thioacetyl to synthesize acylated deoxy glycosides in a one-pot reaction, where the thioacetyl was selectively deacetylated by hydrazine hydrate in DMF within 2-5 min at room temperature, followed by desulfurization under UV light for 1-2 h in the presence of TCEP center dot HCl. The method was then used to synthesize 2-deoxy glycosides with absolute alpha/beta-configuration via stereoselective control of C-2 thioacetate in glycosylation.
• Direct preparation of 2-deoxy-D-glucopyranosides from glucals without Ferrier rearrangement
  作者：Veronique Bolitt、Charles Mioskowski、S. G. Lee、J. R. Falck

  DOI：10.1021/jo00310a006

  日期：1990.11
• Helferich; Iloff, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1933, vol. 221, p. 252,253, 254
  作者：Helferich、Iloff

  DOI：——

  日期：——