(R)-1-((2S,3S,4R,5S)-3,4-bis(benzyloxy)-5-methoxytetrahydrofuran-2-yl)prop-2-en-1-ol | 1083004-99-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-((2S,3S,4R,5S)-3,4-bis(benzyloxy)-5-methoxytetrahydrofuran-2-yl)prop-2-en-1-ol
• CAS: 1083004-99-2
• 化学式: C₂₂H₂₆O₅
• 分子量: 370.445
• InChiKey: KCGGXNMPWUUDPZ-CTWRKMMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-3,4-bis(benzyloxy)-2-((S)-1,2-bis(benzyloxy)ethyl)-3,4-dihydro-2H-pyrrole-1-oxide 、 (R)-1-((2S,3S,4R,5S)-3,4-bis(benzyloxy)-5-methoxytetrahydrofuran-2-yl)prop-2-en-1-ol 以 甲苯 为溶剂， 反应 14.0h， 以64%的产率得到(S)-((2S,3S,4R,5S)-3,4-bis(benzyloxy)-5-methoxytetrahydrofuran-2-yl)((2S,3aS,4S,5S,6S)-4,5-bis(benzyloxy)-6-((S)-1,2-bis(benzyloxy)ethyl)hexahydropyrrolo[1,2-b]isoxazol-2-yl)methanol
  参考文献：
  名称：

  Novel Galf-disaccharide mimics: synthesis by way of 1,3-dipolar cycloaddition reactions in water

  摘要：

  Galactofuranose-disaccharide analogues incorporating a 1,4-dideoxy-1,4-imino-D-galactitol moiety were obtained by 1,3-dipolar cycloadditions of a galacto-configured cyclic nitrone with arabino- or galacto-furanosides carrying a C-vinyl or O-allyl substituent. Remarkably, the cycloadditions could be performed highly efficiently and stereoselectively in water using unprotected nitrone and sugar-derived dipolarophile as reaction partners. The resulting pseudo-disaccharides are analogues of the Galf-Galf motifs found in mycobacterial cell-wall glycans and therefore constitute mimics of the acceptor substrates of mycobacterial Galf-transferases. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.08.006
• 作为产物：
  描述：

  、 乙烯基溴化镁 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 (R)-1-((2S,3S,4R,5S)-3,4-bis(benzyloxy)-5-methoxytetrahydrofuran-2-yl)prop-2-en-1-ol 、
  参考文献：
  名称：

  Novel Galf-disaccharide mimics: synthesis by way of 1,3-dipolar cycloaddition reactions in water

  摘要：

  Galactofuranose-disaccharide analogues incorporating a 1,4-dideoxy-1,4-imino-D-galactitol moiety were obtained by 1,3-dipolar cycloadditions of a galacto-configured cyclic nitrone with arabino- or galacto-furanosides carrying a C-vinyl or O-allyl substituent. Remarkably, the cycloadditions could be performed highly efficiently and stereoselectively in water using unprotected nitrone and sugar-derived dipolarophile as reaction partners. The resulting pseudo-disaccharides are analogues of the Galf-Galf motifs found in mycobacterial cell-wall glycans and therefore constitute mimics of the acceptor substrates of mycobacterial Galf-transferases. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.08.006