1-benzylamino-1,6-dideoxy-D-glucitol-6-C-sulfonic acid | 562075-55-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzylamino-1,6-dideoxy-D-glucitol-6-C-sulfonic acid
• 英文别名: (2S,3S,4R,5S)-6-(benzylamino)-2,3,4,5-tetrahydroxyhexane-1-sulfonic acid
• CAS: 562075-55-2
• 化学式: C₁₃H₂₁NO₇S
• 分子量: 335.378
• InChiKey: SRPXXLINNYSPDF-UMSGYPCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.6
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  156
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-benzylamino-1,6-dideoxy-D-glucitol-6-C-sulfonic acid 在 palladium on activated charcoal 氢气 作用下， 以 水 为溶剂， 反应 12.0h， 以90%的产率得到1-amino-1,6-dideoxy-D-glucitol-6-C-sulfonic acid
  参考文献：
  名称：

  Synthesis of new C-sulfosugars and C-sulfoalditols: Amadori rearrangement of 6-C-sulfo-d-fucose

  摘要：

  The novel 6-deoxy-6-C-sulfo-D-galactose (6-sulfofucose) potassium salt was prepared by oxidation of 1,2,3-tri-O-acetyl-6-S-acetyl-4-O-benzoyl-6-deoxy-alpha-D-galactopyranose with hydrogen peroxide and potassium acetate in acetic acid. Its cyclohexylammonium salt underwent a spontaneous conversion into 1-cyclohexylamino-1,6-dideoxy-D-tagatofuranose-6-C-sulfonic acid 4 through an Amadori rearrangement. 6-Deoxy-6-C-sulfo-D-glucose (sulfoquinovose) and 6-deoxy-6-C-sulfo-D-galactose were transformed into the corresponding 6-deoxy-6-C-sulfoalditols and 1-amino-1,6-dideoxy-6-C-sulfoalditols by reduction and reductive amination, respectively. The alpha anomeric configuration of 4, crystallised as the monohydrate, was assigned by X-ray crystallographic analysis. A conformation between E-5 and T-4(5) for the sugar ring, stabilised by a strong intramolecular hydrogen bond between NH and O-4, was observed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00160-5
• 作为产物：
  描述：

  Potassium; (2S,3S,4R,5S)-6-[(Z)-benzylimino]-2,3,4,5-tetrahydroxy-hexane-1-sulfonate 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 12.0h， 以48%的产率得到1-benzylamino-1,6-dideoxy-D-glucitol-6-C-sulfonic acid
  参考文献：
  名称：

  Synthesis of new C-sulfosugars and C-sulfoalditols: Amadori rearrangement of 6-C-sulfo-d-fucose

  摘要：

  The novel 6-deoxy-6-C-sulfo-D-galactose (6-sulfofucose) potassium salt was prepared by oxidation of 1,2,3-tri-O-acetyl-6-S-acetyl-4-O-benzoyl-6-deoxy-alpha-D-galactopyranose with hydrogen peroxide and potassium acetate in acetic acid. Its cyclohexylammonium salt underwent a spontaneous conversion into 1-cyclohexylamino-1,6-dideoxy-D-tagatofuranose-6-C-sulfonic acid 4 through an Amadori rearrangement. 6-Deoxy-6-C-sulfo-D-glucose (sulfoquinovose) and 6-deoxy-6-C-sulfo-D-galactose were transformed into the corresponding 6-deoxy-6-C-sulfoalditols and 1-amino-1,6-dideoxy-6-C-sulfoalditols by reduction and reductive amination, respectively. The alpha anomeric configuration of 4, crystallised as the monohydrate, was assigned by X-ray crystallographic analysis. A conformation between E-5 and T-4(5) for the sugar ring, stabilised by a strong intramolecular hydrogen bond between NH and O-4, was observed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00160-5