(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((hydroxyimino)(naphthalen-2-yl)methyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1089209-15-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((hydroxyimino)(naphthalen-2-yl)methyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS: 1089209-15-3
• 化学式: C₂₅H₂₇NO₁₀S
• 分子量: 533.556
• InChiKey: OOJUWWMVXNWBPL-ABMICEGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  147.02
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((hydroxyimino)(naphthalen-2-yl)methyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 0.75h， 以36%的产率得到(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-glucitol-spiro[1.5]-3-(2-naphthyl)-1,4,2-oxathiazole
  参考文献：
  名称：

  Novel design principle validated: Glucopyranosylidene-spiro-oxathiazole as new nanomolar inhibitor of glycogen phosphorylase, potential antidiabetic agent

  摘要：

  2-Naphthyl-substituted glucopyranosylidene-spiro-oxathiazole prepared following a novel design principle was found to be the best known glucose analogue inhibitor of rabbit muscle glycogen phosphorylase b (K-i 160 nM). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.052
• 作为产物：
  描述：

  1-硫代-b-D-葡萄糖四乙酸酯 、 N-hydroxy-2-naphthimidoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以78%的产率得到(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((hydroxyimino)(naphthalen-2-yl)methyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Novel design principle validated: Glucopyranosylidene-spiro-oxathiazole as new nanomolar inhibitor of glycogen phosphorylase, potential antidiabetic agent

  摘要：

  2-Naphthyl-substituted glucopyranosylidene-spiro-oxathiazole prepared following a novel design principle was found to be the best known glucose analogue inhibitor of rabbit muscle glycogen phosphorylase b (K-i 160 nM). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.052