1-[(3R,5S)-2-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-3-hydroxymethyl-1,2-isoxazolidin-5-yl]-5-methyl-1H-pyrimidine-2,4-dione | 627486-12-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[(3R,5S)-2-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-3-hydroxymethyl-1,2-isoxazolidin-5-yl]-5-methyl-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(3R,5S)-2-[(3aR,4R,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-(hydroxymethyl)-1,2-oxazolidin-5-yl]-5-methylpyrimidine-2,4-dione
• CAS: 627486-12-8
• 化学式: C₃₃H₄₃N₃O₈Si
• 分子量: 637.805
• InChiKey: NLNDQSLECBHLAV-XPMPNAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-[(3R,5S)-2-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-3-hydroxymethyl-1,2-isoxazolidin-5-yl]-5-methyl-1H-pyrimidine-2,4-dione 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以77%的产率得到1-[(3R,5S)-3-(hydroxymethyl)isoxazolidin-5-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Diastereo- and enantioselective synthesis of N,O-nucleosides

  摘要：

  The diastereo- and enantioselective synthesis of alpha- and beta-3'-hydroxymethyl-N,O-nucleosides is described, based on the 1,3-dipolar cycloaddition of a N-glycosyl nitrone. Two approaches have been evaluated: the one-step procedure, which uses vinyl nucleobases, showed a better stereoselectivity towards beta-nucleosides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00499-3
• 作为产物：
  描述：

  胸腺嘧啶 在 sodium tetrahydroborate 、 N,O-双三甲硅基乙酰胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 反应 6.25h， 生成 1-[(3R,5S)-2-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-3-hydroxymethyl-1,2-isoxazolidin-5-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Diastereo- and enantioselective synthesis of N,O-nucleosides

  摘要：

  The diastereo- and enantioselective synthesis of alpha- and beta-3'-hydroxymethyl-N,O-nucleosides is described, based on the 1,3-dipolar cycloaddition of a N-glycosyl nitrone. Two approaches have been evaluated: the one-step procedure, which uses vinyl nucleobases, showed a better stereoselectivity towards beta-nucleosides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00499-3

文献信息

• Diastereo- and enantioselective synthesis of N,O-nucleosides
  作者：Ugo Chiacchio、Antonino Corsaro、Daniela Iannazzo、Anna Piperno、Venerando Pistarà、Antonio Rescifina、Roberto Romeo、Giovanni Sindona、Giovanni Romeo

  DOI：10.1016/s0957-4166(03)00499-3

  日期：2003.9

  The diastereo- and enantioselective synthesis of alpha- and beta-3'-hydroxymethyl-N,O-nucleosides is described, based on the 1,3-dipolar cycloaddition of a N-glycosyl nitrone. Two approaches have been evaluated: the one-step procedure, which uses vinyl nucleobases, showed a better stereoselectivity towards beta-nucleosides. (C) 2003 Elsevier Ltd. All rights reserved.