3,4,6-tri-O-acetyl-2-deoxy-1-O-o-methylphenyl-α-D-mannopyranoside | 1404295-67-5

• 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-o-methylphenyl-α-D-mannopyranoside
• CAS: 1404295-67-5
• 化学式: C₁₉H₂₄O₈
• 分子量: 380.395
• InChiKey: CPKIIPONKLXXML-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-o-methylphenyl-α-D-mannopyranoside 在 一水合肼 、 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， 反应 0.03h， 以71%的产率得到3,4,6-tri-O-acetyl-2-deoxy-1-O-o-methylphenyl-α-D-mannopyranoside
  参考文献：
  名称：

  A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light To Synthesize Deoxyglycosides

  摘要：

  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.

  DOI：

  10.1021/acs.orglett.9b02033

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。