(2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-carbaldehyde O-(4-methoxy-benzyl)-oxime | 365278-79-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: (2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-carbaldehyde O-(4-methoxy-benzyl)-oxime
• CAS: 365278-79-1
• 化学式: C₁₄H₁₉NO₆
• 分子量: 297.308
• InChiKey: RVDKIGZHQQVLTG-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.32
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  100.74
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-carbaldehyde O-(4-methoxy-benzyl)-oxime 在 盐酸 、 sodium cyanoborohydride 作用下， 以 acetate buffer 为溶剂， 生成 (2R,3S,4S,5R)-2-Hydroxymethyl-5-[(4-methoxy-benzyloxyamino)-methyl]-tetrahydro-furan-3,4-diol
  参考文献：
  名称：

  Mild tagging procedures for the structural analysis of glycans

  摘要：

  The reductive oxyamination of model glycan structures has been investigated as a mild, alternative tagging procedure to reductive amination using O-(4-nitrobenzyl)-hydroxylamine. Grime formation was quantitative, but the reduction step did not always go to completion. Novel O- and N-substituted 7-hydroxycoumaryl- and 3-methoxybenzylhydroxylamines were synthesized and shown to couple quantitatively with model saccharides by oxime formation and reductive hydroxyamination, respectively, under very mild, aqueous conditions. The fluorescent derivatives produced show good chromatographic and mass spectrometric properties. Both procedures are suitable for the labeling of carbohydrates and oligosaccharide fragments from glycosaminoglycan structures, such as heparin and heparan sulfate. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00115-x
• 作为产物：
  描述：

  4-甲氧基苄醇 在 盐酸 、 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 acetate buffer 为溶剂， 反应 3.33h， 生成 (2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-carbaldehyde O-(4-methoxy-benzyl)-oxime
  参考文献：
  名称：

  Mild tagging procedures for the structural analysis of glycans

  摘要：

  The reductive oxyamination of model glycan structures has been investigated as a mild, alternative tagging procedure to reductive amination using O-(4-nitrobenzyl)-hydroxylamine. Grime formation was quantitative, but the reduction step did not always go to completion. Novel O- and N-substituted 7-hydroxycoumaryl- and 3-methoxybenzylhydroxylamines were synthesized and shown to couple quantitatively with model saccharides by oxime formation and reductive hydroxyamination, respectively, under very mild, aqueous conditions. The fluorescent derivatives produced show good chromatographic and mass spectrometric properties. Both procedures are suitable for the labeling of carbohydrates and oligosaccharide fragments from glycosaminoglycan structures, such as heparin and heparan sulfate. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00115-x