(3S,4R,5R,6S)-2,2-bis(hydroxymethyl)-6-(3-(4-methoxybenzyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triol | 1225327-02-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4R,5R,6S)-2,2-bis(hydroxymethyl)-6-(3-(4-methoxybenzyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triol
• CAS: 1225327-02-5
• 化学式: C₂₂H₂₈O₇
• 分子量: 404.46
• InChiKey: GTEOPXNLWAVVJQ-CGXNFDGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.47
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  119.61
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R,6S)-2,2-bis(hydroxymethyl)-6-(3-(4-methoxybenzyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triol 在 吡啶 、 对甲苯磺酰氯 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以15%的产率得到(6S,7R,8R,9S)-6-(3-(4-methoxybenzyl)-4-methylphenyl)-2,5-dioxaspiro[3.5]nonane-7,8,9-triol
  参考文献：
  名称：

  Syntheses of C-5-spirocyclic C-glycoside SGLT2 inhibitors

  摘要：

  Several syntheses of C-5-spirocycle-containing C-glycosides are discussed. A multigram-scale synthesis capitalizing on a one-pot aldol-Cannizzaro sequence is described. Spiro oxetane formation using an unprotected penta-ol C-glycoside as substrate is also exemplified. Functional assessment of these compounds for potency and selectivity was evaluated at human SGLT2 and SGLT1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.024
• 作为产物：
  描述：

  [(3S,4R,5S,6S)-2-(hydroxymethyl)-6-[3-[(4-methoxyphenyl)methyl]-4-methylphenyl]-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol 在 甲酸 、 钯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以97%的产率得到(3S,4R,5R,6S)-2,2-bis(hydroxymethyl)-6-(3-(4-methoxybenzyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Syntheses of C-5-spirocyclic C-glycoside SGLT2 inhibitors

  摘要：

  Several syntheses of C-5-spirocycle-containing C-glycosides are discussed. A multigram-scale synthesis capitalizing on a one-pot aldol-Cannizzaro sequence is described. Spiro oxetane formation using an unprotected penta-ol C-glycoside as substrate is also exemplified. Functional assessment of these compounds for potency and selectivity was evaluated at human SGLT2 and SGLT1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.024