Sulfuric acid mono-{(2R,3S,4S,5R)-3,4-dihydroxy-5-[(4-methoxy-benzyloxyimino)-methyl]-tetrahydro-furan-2-ylmethyl} ester | 365278-80-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Sulfuric acid mono-{(2R,3S,4S,5R)-3,4-dihydroxy-5-[(4-methoxy-benzyloxyimino)-methyl]-tetrahydro-furan-2-ylmethyl} ester
• CAS: 365278-80-4
• 化学式: C₁₄H₁₉NO₉S
• 分子量: 377.372
• InChiKey: MBOPBMDJCUSVNJ-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.49
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  144.11
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Sulfuric acid mono-{(2R,3S,4S,5R)-3,4-dihydroxy-5-[(4-methoxy-benzyloxyimino)-methyl]-tetrahydro-furan-2-ylmethyl} ester 在 盐酸 、 sodium cyanoborohydride 作用下， 以 acetate buffer 为溶剂， 生成 Sulfuric acid mono-{(2R,3S,4S,5R)-3,4-dihydroxy-5-[(4-methoxy-benzyloxyamino)-methyl]-tetrahydro-furan-2-ylmethyl} ester
  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：

  N-(4-methoxybenzyloxy)phthalimide 在 盐酸 、 一水合肼 作用下， 以 甲醇 、 acetate buffer 为溶剂， 反应 3.33h， 生成 Sulfuric acid mono-{(2R,3S,4S,5R)-3,4-dihydroxy-5-[(4-methoxy-benzyloxyimino)-methyl]-tetrahydro-furan-2-ylmethyl} ester
  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