(2S,3S,4S)-2-((S)-1,2-dihydroxyethyl)-3,4-dihydroxy-3,4-dihydro-2H-pyrrole 1-oxide | 1040198-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: (2S,3S,4S)-2-((S)-1,2-dihydroxyethyl)-3,4-dihydroxy-3,4-dihydro-2H-pyrrole 1-oxide
• 英文别名: (2S,3S,4S)-2-[(1S)-1,2-dihydroxyethyl]-1-oxido-3,4-dihydro-2H-pyrrol-1-ium-3,4-diol
• CAS: 1040198-19-3
• 化学式: C₆H₁₁NO₅
• 分子量: 177.157
• InChiKey: OGXHYXTZRMJAOB-BGPJRJDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  110
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-2-((S)-1,2-dihydroxyethyl)-3,4-dihydroxy-3,4-dihydro-2H-pyrrole 1-oxide 、 以 水 为溶剂， 反应 120.0h， 以72%的产率得到(2S,3aS,4S,5S,6S)-6-[(1S)-1,2-dihydroxyethyl]-2-[[(1R)-1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-methoxyoxolan-2-yl]-2-hydroxyethoxy]methyl]-2,3,3a,4,5,6-hexahydropyrrolo[1,2-b][1,2]oxazole-4,5-diol
  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 在 三氯化硼 、 乙醇 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 15.0h， 以91%的产率得到(2S,3S,4S)-2-((S)-1,2-dihydroxyethyl)-3,4-dihydroxy-3,4-dihydro-2H-pyrrole 1-oxide
  参考文献：
  名称：

  通过BCl3介导的脱保护作用的新型多羟基环硝酮和N-羟基吡咯烷。

  摘要：

  提出了一种从其烷氧基（被保护的）衍生物制备新型碳水化合物衍生的对映体纯的多羟基吡咯啉N-氧化物的通用方法。已显示三氯化硼可有效裂解苄基醚和缩酮，而不会影响硝酮的亚胺N-氧化物官能度。相同的试剂（BCl3）还允许有效地合成多羟基化的N-羟基吡咯烷，从而获得了一类新型的N-羟基亚氨基糖。

  DOI：

  10.1021/ol8007759

文献信息

• Novel Galf-disaccharide mimics: synthesis by way of 1,3-dipolar cycloaddition reactions in water
  作者：Virginie Liautard、Valérie Desvergnes、Olivier R. Martin

  DOI：10.1016/j.tetasy.2008.08.006

  日期：2008.9

  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.
• Novel Polyhydroxylated Cyclic Nitrones and <i>N</i>-Hydroxypyrrolidines through BCl₃-Mediated Deprotection
  作者：Stéphanie Desvergnes、Yannick Vallée、Sandrine Py

  DOI：10.1021/ol8007759

  日期：2008.7.17

  method to prepare a new class of carbohydrate-derived, enantiomerically pure polyhydroxypyrroline N-oxides from their alkoxy (protected) derivatives is presented. Boron trichloride is shown to cleave efficiently benzyl ethers and ketals without affecting the imine N-oxide functionality of nitrones. The same reagent (BCl3) also allowed the efficient synthesis of a polyhydroxylated N-hydroxypyrrolidine

  提出了一种从其烷氧基（被保护的）衍生物制备新型碳水化合物衍生的对映体纯的多羟基吡咯啉N-氧化物的通用方法。已显示三氯化硼可有效裂解苄基醚和缩酮，而不会影响硝酮的亚胺N-氧化物官能度。相同的试剂（BCl3）还允许有效地合成多羟基化的N-羟基吡咯烷，从而获得了一类新型的N-羟基亚氨基糖。