5-(tert-butyldiphenylsilyl)-1-deoxy-1-hydroxyamino-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranose | 557794-46-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(tert-butyldiphenylsilyl)-1-deoxy-1-hydroxyamino-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranose
• 英文别名: N-[(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]hydroxylamine
• CAS: 557794-46-4
• 化学式: C₂₄H₃₃NO₅Si
• 分子量: 443.615
• InChiKey: KWDOCVKJAKPALL-GXRSIYKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙醛酸乙酯 、 (R)-(-)-丙烯酰-2,10-樟脑磺内酰胺 、 5-(tert-butyldiphenylsilyl)-1-deoxy-1-hydroxyamino-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranose 以 甲苯 为溶剂， 反应 40.0h， 以57%的产率得到(3R,5R)-2-[5-(tert-butyldiphenylsilyl)-1-deoxy-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranos-1-yl]-5-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatriciclo[5.2.1.0^1,5]decane-4-carbonyl]-isoxazolidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Enantioselective synthesis of 4-hydroxy-d-pyroglutamic acid derivatives by an asymmetric 1,3-dipolar cycloaddition

  摘要：

  The 1,3-dipolar cycloaddition of a chiral nitrone derived from glyoxylic acid and protected D-ribosyl hydroxylamine with the acrylamide of Oppolzer's sultam provides a perfectly stereoselective approach to protected (2R,4R)-4-hydroxy-D-pyro-lutamic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00072-1
• 作为产物：
  描述：

  5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose 在 吡啶 、 盐酸羟胺 作用下， 反应 1.0h， 生成 (4S,5R)-5-[(1R)-2-[[1-(tert-butyl)-1,1-diphenylsilyl]oxy]-1-hydroxyethyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde oxime 、 (4S,5R)-5-[(1R)-2-[[1-(tert-butyl)-1,1-diphenylsilyl]oxy]-1-hydroxyethyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde oxime 、 5-(tert-butyldiphenylsilyl)-1-deoxy-1-hydroxyamino-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranose
  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

• An efficient approach to enantiomeric isoxazolidinyl analogues of tiazofurin based on nitrone cycloadditions
  作者：Pedro Merino、Tomás Tejero、Francisco J. Unzurrunzaga、Santiago Franco、Ugo Chiacchio、Maria G. Saita、Daniela Iannazzo、Anna Piperno、Giovanni Romeo

  DOI：10.1016/j.tetasy.2005.11.004

  日期：2005.11

  An efficient synthetic route to isoxazolidinyl analogues of tiazofurin has been developed. The strategy involves, as a key step, a 1,3-dipolar cycloaddition between acrylonitrile and chiral nonracemic nitrones. An opposite diastereofacial induction was observed when the chiral group was placed at either the carbon atom or the nitrogen one of the nitrone function. The 2-cyano isoxazolidines obtained were further converted into the enantiomeric target compounds by constructing the thiazole ring via condensation with L-cysteine. (c) 2005 Elsevier Ltd. All rights reserved.
• 3-(Aminomethyl)-2-(carboxymethyl)isoxazolidinyl nucleosides: building blocks for peptide nucleic acid analogues
  作者：Pedro Merino、Tomás Tejero、Juan Matés、Ugo Chiacchio、Antonino Corsaro、Giovanni Romeo

  DOI：10.1016/j.tetasy.2007.06.029

  日期：2007.7

  The synthesis of orthogonally protected 3-(aminomethyl)-2-(carboxymethyl)isoxazolidinyl thymine, a convenient monomer for the preparation of novel isoxazolidinyl peptide nucleic acid analogues, has been achieved through enantioselective 1,3-dipolar cyclo-addition between N-glycosyl nitrones and vinyl acetate. (C) 2007 Elsevier Ltd. All rights reserved.
• 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.
• Enantioselective synthesis of 4-hydroxy-d-pyroglutamic acid derivatives by an asymmetric 1,3-dipolar cycloaddition
  作者：Pedro Merino、Julia Revuelta、Tomas Tejero、Ugo Chiacchio、Antonio Rescifina、Anna Piperno、Giovanni Romeo

  DOI：10.1016/s0957-4166(02)00072-1

  日期：2002.2

  The 1,3-dipolar cycloaddition of a chiral nitrone derived from glyoxylic acid and protected D-ribosyl hydroxylamine with the acrylamide of Oppolzer's sultam provides a perfectly stereoselective approach to protected (2R,4R)-4-hydroxy-D-pyro-lutamic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.