(2S,3aS,4S,5S,6S)-6-[(1S)-1,2-bis(phenylmethoxy)ethyl]-2-[[(2S,3S,4R,5S)-5-methoxy-3,4-bis(phenylmethoxy)oxolan-2-yl]methoxymethyl]-4,5-bis(phenylmethoxy)-2,3,3a,4,5,6-hexahydropyrrolo[1,2-b][1,2]oxazole | 1083004-97-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3aS,4S,5S,6S)-6-[(1S)-1,2-bis(phenylmethoxy)ethyl]-2-[[(2S,3S,4R,5S)-5-methoxy-3,4-bis(phenylmethoxy)oxolan-2-yl]methoxymethyl]-4,5-bis(phenylmethoxy)-2,3,3a,4,5,6-hexahydropyrrolo[1,2-b][1,2]oxazole
• CAS: 1083004-97-0
• 化学式: C₅₇H₆₃NO₁₀
• 分子量: 922.128
• InChiKey: CCNXEVXNKCKRGJ-BCHIWPILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  68
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  95.5
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S,3aS,4S,5S,6S)-6-[(1S)-1,2-bis(phenylmethoxy)ethyl]-2-[[(2S,3S,4R,5S)-5-methoxy-3,4-bis(phenylmethoxy)oxolan-2-yl]methoxymethyl]-4,5-bis(phenylmethoxy)-2,3,3a,4,5,6-hexahydropyrrolo[1,2-b][1,2]oxazole 在 copper diacetate 、 溶剂黄146 、 锌 作用下， 以 水 为溶剂， 以76%的产率得到
  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：

  (2S,3S,4S)-3,4-bis(benzyloxy)-2-((S)-1,2-bis(benzyloxy)ethyl)-3,4-dihydro-2H-pyrrole-1-oxide 、 methyl 5-O-allyl-2,3-di-O-dibenzyl-L-arabinofuranoside 以 甲苯 为溶剂， 反应 12.0h， 以49%的产率得到(2S,3aS,4S,5S,6S)-6-[(1S)-1,2-bis(phenylmethoxy)ethyl]-2-[[(2S,3S,4R,5S)-5-methoxy-3,4-bis(phenylmethoxy)oxolan-2-yl]methoxymethyl]-4,5-bis(phenylmethoxy)-2,3,3a,4,5,6-hexahydropyrrolo[1,2-b][1,2]oxazole
  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