(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-2-acetoxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-8,10-dione | 227458-61-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6R)-3,4,5-triacetoxy-2-acetoxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-8,10-dione
• 英文别名: [(5R,7R,8R,9S,10R)-8,9,10-triacetyloxy-2,4-dioxo-6-oxa-1,3-diazaspiro[4.5]decan-7-yl]methyl acetate
• CAS: 227458-61-9
• 化学式: C₁₆H₂₀N₂O₁₁
• 分子量: 416.342
• InChiKey: LVEMWMDGBPYQMX-GUYIQFIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  173
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-3,4,5-triacetoxy-2-acetoxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-8,10-dione 在 甲醇 、 sodium methylate 作用下， 以72%的产率得到(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-2-hydroxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-8,10-dione
  参考文献：
  名称：

  Synthesis of and a Comparative Study on the Inhibition of Muscle and Liver Glycogen Phosphorylases by Epimeric Pairs of d-Gluco- and d-Xylopyranosylidene-spiro-(thio)hydantoins and N-(d-Glucopyranosyl) Amides

  摘要：

  D-Gluco- and D-xylopyranosylidene-spiro-hydantoins and -thiohydantoins were prepared from the parent sugars in a six-step, highly chemo-, regio-, and stereoselective procedure. In the key step of the syntheses C-(1-bromo-1-deoxy-beta -D-glycopyranosyl)formamides were reacted with cyanate ion to give spiro-hydantoins with a retained configuration at the anomeric center as the major products. On the other hand, thiocyanate ions gave spiro-thiohydantoins with an inverted anomeric carbon as the only products. On the basis of radical inhibition studies, a mechanistic rationale was proposed to explain this unique stereoselectivity and the formation of C-(1-hydroxy-beta -D-glycopyranosyl)formamides as byproducts. Enzyme assays with a and b forms of muscle and liver glycogen phosphorylases showed spiro-hydantoin 12 and spiro-thiohydantoin 14 to be the best and equipotent inhibitors with K-i values in the low micromolar range. The study of epimeric pairs of D-gluco and D-Xylo configurated spiro-hydantoins and N-(D-glucopyranosyl)amides corroborated the role of specific hydrogen bridges in binding the inhibitors to the enzyme.

  DOI：

  10.1021/jm010892t
• 作为产物：
  描述：

  C-(2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranosyl)formamide 在 silver cyanate 作用下， 以 硝基甲烷 为溶剂， 以19%的产率得到C-(2,3,4,6-tetra-O-acetyl-1-hydroxy-β-D-glucopyranosyl)formamide
  参考文献：
  名称：

  Efficient inhibition of muscle and liver glycogen phosphorylases by a new glucopyranosylidene-spiro-thiohydantoin

  摘要：

  Reaction of C-(1-bromo-1-deoxy-beta-D-glucopyranosyl)forma 2 with thiocyanate ions was the key step of a short synthesis of D-glucopyranosylidene-spiro-thiohydantoin 7 which proved to be a potent inhibitor of muscle and liver glycogen phosphorylases. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00192-4