((2R,3S,6S)-3-acetoxy-6-(1,3-dioxoisoindolin-2-yl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate | 1355954-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: ((2R,3S,6S)-3-acetoxy-6-(1,3-dioxoisoindolin-2-yl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate
• 英文别名: 1-{4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl}-phthalimide；[(2R,3S,6S)-3-acetyloxy-6-(1,3-dioxoisoindol-2-yl)-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1355954-67-4
• 化学式: C₁₈H₁₇NO₇
• 分子量: 359.335
• InChiKey: MULIPEXKQUEXMY-XHSDSOJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  99.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  ((2R,3S)-3-acetoxy-6-hydroxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 N,N'-二环己基碳二亚胺 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.5h， 生成 ((2R,3S,6S)-3-acetoxy-6-(1,3-dioxoisoindolin-2-yl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate
  参考文献：
  名称：

  Palladium-Catalyzed Glycosylation: Novel Synthetic Approach to Diverse N-Heterocyclic Glycosides

  摘要：

  An efficient and highly stereoselective method for the construction of N-heterocyclic glycosides is reported. This method is based on a palladium-catalyzed allylation which proceeded to provide N-heterocyclic glycosyl compounds in good-to-excellent yields with beta- or alpha-selectivity. Various N-nucleophiles were examined for this reaction and selected N-glycosyl isatin substrates were further elaborated to bis-indole sugars which have potential as antiproliferative drugs.

  DOI：

  10.1021/ol5037437

文献信息

• O- and N-Glycosidation of d-glycals using Ferrier rearrangement under Mitsunobu reaction conditions. Application to N-nucleoside synthesis
  作者：Kyosuke Michigami、Masahiko Hayashi

  DOI：10.1016/j.tet.2011.11.084

  日期：2012.1

  We have disclosed the reaction of 3-hydroxy free glycals with O- or N-nucleophiles under Mitsunobu reaction conditions proceeded to produce 2,3-unsaturated glycosides in good to high yield and moderate stereoselectivity. The reaction would take place via allyloxycarbenium ion. (C) 2011 Elsevier Ltd. All rights reserved.