2,6-anhydro-3,7-di-O-benzyl-4,5-di-O-(p-methoxybenzyl)-1-deoxy-D-glucohept-1-enitol | 314253-00-4

• 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: 2,6-anhydro-3,7-di-O-benzyl-4,5-di-O-(p-methoxybenzyl)-1-deoxy-D-glucohept-1-enitol
• CAS: 314253-00-4
• 化学式: C₃₇H₄₀O₇
• 分子量: 596.72
• InChiKey: GDUMEEORVADQQB-LADGJGSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.89
• 重原子数：
  44.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,6-anhydro-3,7-di-O-benzyl-4,5-di-O-(p-methoxybenzyl)-1-deoxy-D-glucohept-1-enitol 在 9-borabicyclo[3.3.1]nonane dimer 、 氢氧化钾 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以58%的产率得到2,6-di-O-benzyl-3,4-di-O-(p-methoxybenzyl)-β-D-glucopyranosylmethanol
  参考文献：
  名称：

  C-Glycoside based mimics of d-myo-inositol 1,4,5-trisphosphate

  摘要：

  Epimeric C-glycoside based polyphosphates, alpha- and beta-D-glucopyranosylmethanol 3,4,1'-trisphosphates (8 and 9) were prepared from D-glucose. The key intermediate, allyl 2,6-di-O-benzyl-alpha-D-glucopyranoside, was prepared in five steps (67% yield) from allyl alpha-D-glucopyranoside without the need for chromatography. Compounds 8 and 9 were shown to be full agonists at the Ins(1,4,5)P-3 receptors of permeabilised hepatocytes, but with markedly different potencies. Such C-glycoside analogues are worthy of further development as Ins(1,4,5)P-3 receptor ligands. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00175-0
• 作为产物：
  描述：

  (2S,3R,4S,5R,6R)-2-Allyloxy-3-benzyloxy-6-benzyloxymethyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran 在 吡啶 、 甲醇 、 草酰氯 、 二甲基亚砜 、 palladium dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.83h， 生成 2,6-anhydro-3,7-di-O-benzyl-4,5-di-O-(p-methoxybenzyl)-1-deoxy-D-glucohept-1-enitol
  参考文献：
  名称：

  C-Glycoside based mimics of d-myo-inositol 1,4,5-trisphosphate

  摘要：

  Epimeric C-glycoside based polyphosphates, alpha- and beta-D-glucopyranosylmethanol 3,4,1'-trisphosphates (8 and 9) were prepared from D-glucose. The key intermediate, allyl 2,6-di-O-benzyl-alpha-D-glucopyranoside, was prepared in five steps (67% yield) from allyl alpha-D-glucopyranoside without the need for chromatography. Compounds 8 and 9 were shown to be full agonists at the Ins(1,4,5)P-3 receptors of permeabilised hepatocytes, but with markedly different potencies. Such C-glycoside analogues are worthy of further development as Ins(1,4,5)P-3 receptor ligands. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00175-0