2-amino-N-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)malondiamide | 168906-85-2

• 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: 2-amino-N-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)malondiamide
• 英文别名: [(3aR,4R,6R,6aR)-4-[(2,3-diamino-3-oxopropanoyl)amino]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl acetate
• CAS: 168906-85-2
• 化学式: C₁₃H₂₁N₃O₇
• 分子量: 331.326
• InChiKey: BERAJBGAVZRZNU-LYECJJOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  152
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethylformimidate hydrochloride 、 2-amino-N-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)malondiamide 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以69%的产率得到((3aR,4R,6R,6aR)-6-(4-carbamoyl-5-hydroxy-1H-imidazol-1-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl acetate
  参考文献：
  名称：

  A Novel Synthesis of Mizoribine® and Related Nucleosides from Acyclic Precursors

  摘要：

  Mizoribine(R) (4-carbamoyl-1-beta-D-ribofuranosylimidazolium-5-olate)(13 beta) and its 4-cyano analogue (20) were synthesized by formation of a malonamide from 2,3-isopropylidene-D-ribosylamine and a malonic acid derivative followed by amination, cyclisation and deprotection steps.

  DOI：

  10.1080/15257779508012385
• 作为产物：
  描述：

  Acetic acid (3aR,4R,6aR)-6-{2-carbamoyl-2-[(E)-hydroxyimino]-acetylamino}-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 在 水 、 氢化铝 、 汞 作用下， 以10%的产率得到2-amino-N-(5-O-acetyl-2,3-O-isopropylidene-α-D-ribofuranosyl)malondiamide
  参考文献：
  名称：

  A Novel Synthesis of Mizoribine® and Related Nucleosides from Acyclic Precursors

  摘要：

  Mizoribine(R) (4-carbamoyl-1-beta-D-ribofuranosylimidazolium-5-olate)(13 beta) and its 4-cyano analogue (20) were synthesized by formation of a malonamide from 2,3-isopropylidene-D-ribosylamine and a malonic acid derivative followed by amination, cyclisation and deprotection steps.

  DOI：

  10.1080/15257779508012385

文献信息

• A synthesis of bredinin (Mizoribine®) from an acyclic precursor
  作者：Robert W. Humble、Danielle F. Middleton、Joseph Banoub、David F. Ewing、Andrew N. Boa、Grahame Mackenzie

  DOI：10.1016/j.tetlet.2011.09.085

  日期：2011.11

  Bredinin (4-carbamoyl-1-beta-D-ribofuranosylimidazolium-5-olate, 1) was synthesised by the formation of a malonamate from 2,3-isopropylidene-D-ribofuranosylamine and ethyl malonyl chloride, followed by a sequence involving amination, via reduction of an oxime, heterocycle formation and then deprotection. (C) 2011 Elsevier Ltd. All rights reserved.