methyl 3-O-acetyl-1,2-O-isopropylidene-α-D-ribofuranuronate | 1076189-26-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-acetyl-1,2-O-isopropylidene-α-D-ribofuranuronate
• CAS: 1076189-26-8
• 化学式: C₁₁H₁₆O₇
• 分子量: 260.244
• InChiKey: ZUXGZHZERGFDBX-IBCQBUCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.03
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 3-O-acetyl-1,2-O-isopropylidene-α-D-ribofuranuronate 、 甲胺 以 四氢呋喃 为溶剂， 反应 24.0h， 以96.6%的产率得到N-methyl-1,2-O-isopropylidene-α-D-ribofuranuronamide
  参考文献：
  名称：

  Synthesis of N-methyl-d-ribopyranuronamide nucleosides

  摘要：

  The Synthesis of N-methyl-D-ribopyranuronamide nucleosides is described. The key route is the rearrangement of a 1,2-O-isopropylidene protected furanose sugar with a carboxamide function in the 4-position to a ribopyranuronamide ring. The Lewis acid catalyzed condensation of adenine and thymine nucleobases with the per-O-acetylated N-methyl-D-ribopyranuronamide sugar is used to give the target nucleosides as a mixture of the alpha and beta anomers. The mixture was separated and the final Compounds were obtained by deacetylation in basic conditions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.027
• 作为产物：
  描述：

  甲醇 、 3-O-acetyl-1,2-O-isopropylidene-α-D-ribofuranuronic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 反应 24.0h， 以76.9%的产率得到methyl 3-O-acetyl-1,2-O-isopropylidene-α-D-ribofuranuronate
  参考文献：
  名称：

  Synthesis of N-methyl-d-ribopyranuronamide nucleosides

  摘要：

  The Synthesis of N-methyl-D-ribopyranuronamide nucleosides is described. The key route is the rearrangement of a 1,2-O-isopropylidene protected furanose sugar with a carboxamide function in the 4-position to a ribopyranuronamide ring. The Lewis acid catalyzed condensation of adenine and thymine nucleobases with the per-O-acetylated N-methyl-D-ribopyranuronamide sugar is used to give the target nucleosides as a mixture of the alpha and beta anomers. The mixture was separated and the final Compounds were obtained by deacetylation in basic conditions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.027