3,4,6-tri-O-acetyl-β-D-glucopyranose 1,2-(tert-butyl orthoacetate) | 117708-92-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3,4,6-tri-O-acetyl-β-D-glucopyranose 1,2-(tert-butyl orthoacetate)
• 英文别名: [(3aS,5R,6R,7S,7aR)-6,7-diacetyloxy-2-methyl-2-[(2-methylpropan-2-yl)oxy]-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate
• CAS: 117708-92-6
• 化学式: C₁₈H₂₈O₁₀
• 分子量: 404.414
• InChiKey: CPHHOBDQMIXIDV-WCRYKSFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-β-D-glucopyranose 1,2-(tert-butyl orthoacetate) 在 甲醇 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (3aS,5R,6S,7S,7aR)-5-(hydroxymethyl)-2-methyl-2-[(2-methylpropan-2-yl)oxy]-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-6,7-diol
  参考文献：
  名称：

  Preference for Glucose over Inositol Headgroup during Lysolipid Activation of G Protein-Coupled Receptor 55

  摘要：

  G protein-coupled receptor 55 (GPR55) is highly expressed in brain and chemorepulsion peripheral nervous system. Originally deorphanized as a cannabinoid receptor, recently GPRS5 has been described as a lysophospholipid-responsive receptor, specifically toward lysophosphatidylinositol and lysophosphatidyl-beta-n-glucoside (LysoPtdGlc). To characterize lysolipid-GPR55 interaction, synthetic access to LysoPtdGlc and selected analogues was established utilizing a phosphorus(III)-based chemical approach. The biological activity of each synthetic lipid was assessed using a GPR55-dependent chemotropism assay in primary sensory neurons. Combined with molecular dynamics simulations the potential ligand entry port and binding pocket specifics are discussed. These results highlight the preference for gluco- over inositol- and galacto-configured headgroups.

  DOI：

  10.1021/acschemneuro.8b00505

文献信息

• Semisynthetic analogues of ginsenosides, glycosides from ginseng
  作者：Lyubov N. Atopkina、Vladimir A. Denisenko、Nina I. Uvarova、Georgi B. Elyakov

  DOI：10.1016/0008-6215(88)85045-6

  日期：1988.6

  Abstract Glycosylation of the dammar-24-ene-3,12β,20( S )-triols with 2,3,4,6-tetra- O -acetyl-α- d -glucopyranosyl bromide ( A ) in the presence of silver oxide in dichloro-methane gives a mixture of the acetylated 3-, 12-, 20-, 3,12-di-, and 3,20-di- O -β- d -glucopyranosyl derivatives in a total yield of 83–84.5%. Under similar conditions, the 3- O -acetyl derivatives of dammar-24-ene-3,12β,20(

  摘要在氧化银存在的条件下，将dammar-24-ene-3,12β，20（S）-三醇与2,3,4,6-四-O-乙酰基-α-d-吡喃葡萄糖基溴化物（A）糖基化二氯甲烷中得到乙酰化的3-，12-，20-，3,12-二-和3,20-二-O-β-d-吡喃葡萄糖基衍生物的混合物，总产率为83-84.5％ 。在相似的条件下，达玛-24-烯-3,12β，20（S）-三醇的3-O-乙酰基衍生物得到12-和20-O-β-d-吡喃葡萄糖基衍生物的混合物。在氰化汞存在的条件下，在硝化甲烷中，将异黄酮三醇[dammar-24-ene-3α，12β，20（S）-三醇]与糖基溴化物A和3,4,6-三-O-乙酰基-β缩合-在2,4存在下的d-吡喃葡萄糖1,2-（原乙酸叔丁酯）