C-(2,3,4,6-tetra-O-acetyl-1-hydroxy-β-D-glucopyranosyl)formamide | 223261-80-1

• 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: C-(2,3,4,6-tetra-O-acetyl-1-hydroxy-β-D-glucopyranosyl)formamide
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-carbamoyl-6-hydroxyoxan-2-yl]methyl acetate
• CAS: 223261-80-1
• 化学式: C₁₅H₂₁NO₁₁
• 分子量: 391.332
• InChiKey: UQCDSFPUJABSNF-ZHZXCYKASA-N

物化性质

• 熔点：
  177-179 °C
• 沸点：
  540.152±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.416±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  178
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  C-(2,3,4,6-tetra-O-acetyl-1-hydroxy-β-D-glucopyranosyl)formamide 在 甲醇 、 sodium methylate 作用下， 以68%的产率得到C-(1-hydroxy-β-D-glucopyranosyl)formamide
  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：

  2,3,4,6-tetra-O-acetyl-1-deoxy-1-bromo-β-D-glycopyranosyl cyanide 在 水 、 四氯化钛 、 溶剂黄146 、 silver(l) oxide 作用下， 以 二甲基亚砜 为溶剂， 反应 144.0h， 生成 C-(2,3,4,6-tetra-O-acetyl-1-hydroxy-β-D-glucopyranosyl)formamide
  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

文献信息

• Novel glycosylidene-spiro-heterocycles from unprecedented solvent incorporation in Koenigs–Knorr-like reactions of C-(1-bromo-1-deoxy-β-D-glycopyranosyl)formamides
  作者：László Somsák、László Kovács、Viktor Gyóllai、Erzsébet Ősz

  DOI：10.1039/a900082h

  日期：——

  The title compounds give glycopyranosylidene-spiro-dioxolanes 3 and 4 in acetone and C-(1-methylsulfanylmethoxy-α-D-glycopyranosyl)formamides 5 in DMSO in the presence of Ag2CO3 and AgF, respectively.

  在 Ag2CO3 和 AgF 的存在下，标题化合物在丙酮中分别生成了吡喃葡萄糖基亚螺二氧戊环 3 和 4，在二甲基亚砜中生成了 C-(1-甲硫基甲氧基-δ-±-D-吡喃葡萄糖基)甲酰胺 5。
• Efficient inhibition of muscle and liver glycogen phosphorylases by a new glucopyranosylidene-spiro-thiohydantoin
  作者：Erzsébet Ősz、László Somsák、László Szilágyi、László Kovács、Tibor Docsa、Béla Tóth、Pál Gergely

  DOI：10.1016/s0960-894x(99)00192-4

  日期：1999.5

  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.