((2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-nitro-2-(prop-2-ynyloxy)-tetrahydro-2H-pyran-3-yl)methyl acetate | 1257639-95-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-nitro-2-(prop-2-ynyloxy)-tetrahydro-2H-pyran-3-yl)methyl acetate
• 英文别名: [(2S,3R,4R,5R,6R)-3-nitro-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-prop-2-ynoxyoxan-3-yl]methyl acetate
• CAS: 1257639-95-4
• 化学式: C₃₃H₃₅NO₉
• 分子量: 589.642
• InChiKey: MUTRRFBZIXSPHI-ISBPOBPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ((2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-nitro-2-(prop-2-ynyloxy)-tetrahydro-2H-pyran-3-yl)methyl acetate 在 偶氮二异丁腈 、 10% palladium on activated carbon 、 氢气 、 三正丁基氢锡 作用下， 以 乙醇 、 苯 为溶剂， 反应 53.0h， 生成 [(3R,3aS,4R,5R,6R,7aS)-4,5-dihydroxy-6-(hydroxymethyl)-3-(2-phenylethyl)-2,3,4,5,6,7a-hexahydrofuro[2,3-b]pyran-3a-yl]methyl acetate
  参考文献：
  名称：

  Chemistry of 2-Nitroglycals: A One-Pot Three-Component Stereoselective Approach toward 2-C-Branched O-Galactosides

  摘要：

  A convenient one-pot three-component approach for the synthesis of 2-C-branched O-glycosides has been developed from 2-nitroglycals. These 2-C-branched sugars have been shown to be precursors for a variety of biologically and synthetically relevant molecules.

  DOI：

  10.1021/jo101735u
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-2-nitro-D-galactal 在 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 ((2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-nitro-2-(prop-2-ynyloxy)-tetrahydro-2H-pyran-3-yl)methyl acetate
  参考文献：
  名称：

  Chemistry of 2-Nitroglycals: A One-Pot Three-Component Stereoselective Approach toward 2-C-Branched O-Galactosides

  摘要：

  A convenient one-pot three-component approach for the synthesis of 2-C-branched O-glycosides has been developed from 2-nitroglycals. These 2-C-branched sugars have been shown to be precursors for a variety of biologically and synthetically relevant molecules.

  DOI：

  10.1021/jo101735u