3,4,6-tri-O-acetyl-2-deoxy-1-O-p-methylphenyl-α-D-mannopyranoside | 38223-17-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-1-O-p-methylphenyl-α-D-mannopyranoside
• 英文别名: p-tolyl-(tri-O-acetyl-α-D-arabino-2-deoxy-hexopyranoside)；p-Tolyl-(tri-O-acetyl-α-D-arabino-2-desoxy-hexopyranosid)
• CAS: 38223-17-5
• 化学式: C₁₉H₂₄O₈
• 分子量: 380.395
• InChiKey: PHSMBPFPUIVRFK-YRXWBPOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-S-acetyl-1-O-p-methylphenyl-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3,4,6-tri-O-acetyl-2-deoxy-1-O-p-methylphenyl-α-D-mannopyranoside
  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

• 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.
• 926. The preparation and properties of aryl 2-deozy-α-<scp>D</scp>-glucopyranosides
  作者：F. Shafizadeh、M. Stacey

  DOI：10.1039/jr9570004612

  日期：——
• Thermolysis of phenyl glycosides
  作者：Fred Shafizadeh、Makram H. Meshreki、Ronald A. Susott

  DOI：10.1021/jo00946a027

  日期：1973.3