1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dihydropyridin-2-one | 17430-67-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dihydropyridin-2-one
• 英文别名: (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-oxopyridin-1(2H)-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate；5-Jod-1-(tetraacetyl-1-β-D-glucosyl)-pyridon-2；1-(Tetraacetyl-1-β-D-glucosyl)-pyridon-(2), 1-(Tetra-O-acetyl-β-D-glucosyl)-pyridon-(2)；1-Tetra-O-acetyl-β-D-glucopyranosyl-pyridon(2)；1-(Tetraacetyl-1-β-D-glucosyl)-pyridon-(2), 1-(Tetra-O-acetyl-β-D-glucopyranosyl)-pyridon-(2)；1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-2(1H)-pyridon；1-(Tetraacetyl-1-β-D-glucosyl)-pyridon-(2)；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(2-oxopyridin-1-yl)oxan-2-yl]methyl acetate
• CAS: 17430-67-0
• 化学式: C₁₉H₂₃NO₁₀
• 分子量: 425.392
• InChiKey: FJXHXAWLSTUDPR-IQZDNPOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-羟基吡啶 、 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 在 N,O-双(三甲基硅烷基)三氟乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以95%的产率得到1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,4-dihydropyridin-2-one
  参考文献：
  名称：

  An improved procedure for nucleoside synthesis using glycosyl trifluoroacetimidates as donors

  摘要：

  Using glycosyl trifluoroacetimidates as donors and nitromethane (or acetonitrile) as solvent, silylation and subsequent glycosylation were realized in a 'one-pot' procedure to provide the corresponding nucleosides derivatives in high yields.[GRAPHICS](C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.03.010

文献信息

• Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction
  作者：Chengyuan Liang、Weihui Ju、Shunjun Ding、Han Sun、Gennian Mao

  DOI：10.3390/molecules22010084

  日期：——

  An effective synthesis of nucleosides using glycosyl chlorides as glycosyl donors in the absence of Lewis acid has been developed. Glycosyl chlorides have been shown to be pivotal intermediates in the classical silyl-Hilbert-Johnson reaction. A possible mechanism that differs from the currently accepted mechanism advanced by Vorbrueggen has been proposed and verified by experiments. In practice, this

  已经开发了在不存在路易斯酸的情况下使用糖基氯化物作为糖基供体的有效的核苷合成方法。糖基氯已被证明是经典的甲硅烷基-希尔伯特-约翰逊反应中的关键中间体。已经提出了一种可能的机制，该机制与Vorbrueggen提出的当前接受的机制不同，并通过实验进行了验证。实际上，这种无催化剂的方法可轻松轻松地获得卡培他滨。
• Effective synthesis of nucleosides with glycosyl trifluoroacetimidates as donors
  作者：Jinxi Liao、Jiansong Sun、Biao Yu

  DOI：10.1016/j.tetlet.2008.06.042

  日期：2008.8

  Glycosyl trifluoroacetimidates have been disclosed to be effective glycosyl donors for the synthesis of nucleosides; the present N-glycosylation protocol requires only a catalytic amount of TMSOTf as promoter and proceeds smoothly at room temperature. (c) 2008 Elsevier Ltd. All rights reserved.