Sulfuric acid mono-[6-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexyl] ester | 178872-62-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Sulfuric acid mono-[6-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexyl] ester
• 英文别名: 6-[(2R,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxyhexyl hydrogen sulfate
• CAS: 178872-62-3
• 化学式: C₃₃H₄₂O₉S
• 分子量: 614.757
• InChiKey: RSLXFEIAFZWISO-GXCPKCQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  43.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  109.75
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Sulfuric acid mono-[6-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexyl] ester 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 以74.9%的产率得到Sulfuric acid mono-[6-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexyl] ester
  参考文献：
  名称：

  Synthesis of Sialyl Lewis X Analogues

  摘要：

  Sialyl Lewis X (SLe(x)) analogs 2a and 2b were synthesised, where the N-acetyl-D-glucose and the D-galactose units of SLe(x) 1 were replaced with an alkyl and a heteroalkyl spacer. Sulphate ester 6i was also synthesised from alcohol 6b and chlorosulphonic acid. A novel promoter. silver mercaptoethanesulphonate. was used to synthesise alpha-sialosides 2c, 7b and 7c.

  DOI：

  10.1080/07328309608005661
• 作为产物：
  描述：

  perbenzyl fucosyl bromide 在 吡啶 、 氯磺酸 、 4 A molecular sieve 、 四乙基溴化铵 作用下， 以 乙腈 为溶剂， 反应 75.0h， 生成 Sulfuric acid mono-[6-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexyl] ester
  参考文献：
  名称：

  Synthesis of Sialyl Lewis X Analogues

  摘要：

  Sialyl Lewis X (SLe(x)) analogs 2a and 2b were synthesised, where the N-acetyl-D-glucose and the D-galactose units of SLe(x) 1 were replaced with an alkyl and a heteroalkyl spacer. Sulphate ester 6i was also synthesised from alcohol 6b and chlorosulphonic acid. A novel promoter. silver mercaptoethanesulphonate. was used to synthesise alpha-sialosides 2c, 7b and 7c.

  DOI：

  10.1080/07328309608005661