(3'R,5'S)-1-[2'-(5''-O-tert-butyldiphenylsilyl-2'',3''-O-isopropylidene-β-D-ribofuranosyl)-3'-ethoxycarbonyl-1',2'-isoxazolidinyl]thymine | 256949-49-2

• 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: (3'R,5'S)-1-[2'-(5''-O-tert-butyldiphenylsilyl-2'',3''-O-isopropylidene-β-D-ribofuranosyl)-3'-ethoxycarbonyl-1',2'-isoxazolidinyl]thymine
• 英文别名: 1-[(3R,5S)-2-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-3-ethoxycarbonyl-1,2-isoxazolidin-5-yl]-5-methyl-1H-pyrimidine-2,4(1H,3H)-dione；ethyl (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]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-1,2-oxazolidine-3-carboxylate
• CAS: 256949-49-2
• 化学式: C₃₅H₄₅N₃O₉Si
• 分子量: 679.843
• InChiKey: REMKVGWVORSETR-UKJKCSSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  48
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (3'R,5'S)-1-[2'-(5''-O-tert-butyldiphenylsilyl-2'',3''-O-isopropylidene-β-D-ribofuranosyl)-3'-ethoxycarbonyl-1',2'-isoxazolidinyl]thymine 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 5.0h， 以72%的产率得到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
• 作为产物：
  描述：

  (4S,5R)-5-[(1R)-2-[[1-(tert-butyl)-1,1-diphenylsilyl]oxy]-1-hydroxyethyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde oxime 在 牛血清白蛋白 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 15.25h， 生成 (3'R,5'S)-1-[2'-(5''-O-tert-butyldiphenylsilyl-2'',3''-O-isopropylidene-β-D-ribofuranosyl)-3'-ethoxycarbonyl-1',2'-isoxazolidinyl]thymine
  参考文献：
  名称：

  Homochiral α-d- and β-d-Isoxazolidinylthymidines via 1,3-Dipolar Cycloaddition

  摘要：

  The introduction of chiral auxiliaries at the C- or N-atom in starting nitrones has been investigated as a stereoselective synthetic route to heterocyclic nucleoside analogues. The carbohydrate auxiliary at nitrogen atom gave the best results, thus allowing an easy and enantioselective synthesis of isoxazolidinyl thymine 26.

  DOI：

  10.1021/jo990576a

文献信息

• Homochiral α-<scp>d</scp>- and β-<scp>d</scp>-Isoxazolidinylthymidines via 1,3-Dipolar Cycloaddition
  作者：Ugo Chiacchio、Antonino Corsaro、Giuseppe Gumina、Antonio Rescifina、Daniela Iannazzo、Anna Piperno、Giovanni Romeo、Roberto Romeo

  DOI：10.1021/jo990576a

  日期：1999.12.1

  The introduction of chiral auxiliaries at the C- or N-atom in starting nitrones has been investigated as a stereoselective synthetic route to heterocyclic nucleoside analogues. The carbohydrate auxiliary at nitrogen atom gave the best results, thus allowing an easy and enantioselective synthesis of isoxazolidinyl thymine 26.
• 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.