β-1-methoxy-2,3,4,6-O-acetyl-L-glucose | 934714-21-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: β-1-methoxy-2,3,4,6-O-acetyl-L-glucose
• 英文别名: methyl β-L-glucopyranoside tetraacetate；β-L-1-methoxy-2,3,4,6-O-acetylglucose；methyl-(tetra-O-acetyl-β-L-glucopyranoside)；Methyl-(tetra-O-acetyl-β-L-glucopyranosid)；[(2S,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-methoxyoxan-2-yl]methyl acetate
• CAS: 934714-21-3
• 化学式: C₁₅H₂₂O₁₀
• 分子量: 362.334
• InChiKey: UYWUMFGDPBMNCA-RMEBNNNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  β-1-methoxy-2,3,4,6-O-acetyl-L-glucose 在 氯仿 、 三氟化硼 作用下， 生成 α-1-methoxy-2,3,4,6-O-acetyl-L-glucose
  参考文献：
  名称：

  乙酰化烷基吡喃糖苷异构化的机制

  摘要：

  明确的证据表明乙酰化烷基吡喃糖苷的异构化可以通过分子内机制进行，这是通过观察到 β-吡喃葡萄糖苷四乙酸甲酯与在甲氧基基团中标记的 D-异构体的外消旋混合物与碳 14 异构化而获得的四氯化钛和三氟化硼，而不会将放射性甲氧基转移到 L-异构体上。据认为，这些分子内异构化是最好的合理化结果，因为环境尝试导致糖苷裂解并通过离子对中间体进行，其中阴离子来自苷元基团，但未成功。

  DOI：

  10.1139/v55-015
• 作为产物：
  描述：

  L-(-)-glucose 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 作用下， 反应 36.0h， 生成 β-1-methoxy-2,3,4,6-O-acetyl-L-glucose
  参考文献：
  名称：

  Caminoside A, an Antimicrobial Glycolipid Isolated from the Marine Sponge Caminus sphaeroconia

  摘要：

  [GRAPHICS]Extracts of the marine sponge Caminus sphaeroconia showed potent activity in a screen for bacterial type III secretion inhibitors. Bioassay guided fractionation of the extract led to the isolation of the novel antimicrobial glycollpid caminoside A (1). The structure of caminoside A was elucidated by analysis of spectroscopic data and chemical degradation.

  DOI：

  10.1021/ol0268337

文献信息

• Antimycobacterial 1,4-napthoquinone natural products from Moneses uniflora
  作者：Haoxin Li、Allyson Bos、Stéphanie Jean、Duncan Webster、Gilles A. Robichaud、John A. Johnson、Christopher A. Gray

  DOI：10.1016/j.phytol.2018.07.032

  日期：2018.10

  new 1,4-naphthoquinone derivative, 5,8-dihydro-3-hydroxychimaphilin (4) and five known compounds (1, 2 and 5-7) were isolated from an extract of the Canadian medicinal plant Moneses uniflora that significantly inhibited the growth of Mycobacterium tuberculosis H37Ra. The structure of 4 was established through analysis of NMR and MS data and the absolute configuration of the glycone of 5 was determined by chemical transformation and comparison with standards prepared from D- and L-glucose. All compounds isolated were screened against Mycobacterium tuberculosis (H37Ra) and the mammalian HEK 293 cell line and, with the exception of compounds 5 and 7, exhibited marked selectivity in their bioactivity: Compound 1 exhibited potent antimycobacterial activity (IC50 of 5.4 mu M) and moderate cytotoxicity (IC50 of 30 mu M); compounds 2, 4 and 6 showed moderate antimycobacterial activity (IC50 values from 28 to 47 mu M) without affecting the viability of mammalian cells; compound 5 displayed moderate activity in both assays (IC50 values of 44 and 55 mu M respectively); and compound 7 was not active in either assay. These data suggest that the Moneses napthaquinone derivatives elicit biological responses in mycobacterial and mammalian cells through disparate modes of action that warrant further investigation.
• Caminoside A, an Antimicrobial Glycolipid Isolated from the Marine Sponge <i>Caminus sphaeroconia</i>
  作者：Roger G. Linington、Marilyn Robertson、Annick Gauthier、B. Brett Finlay、Rob van Soest、Raymond J. Andersen

  DOI：10.1021/ol0268337

  日期：2002.11.1

  [GRAPHICS]Extracts of the marine sponge Caminus sphaeroconia showed potent activity in a screen for bacterial type III secretion inhibitors. Bioassay guided fractionation of the extract led to the isolation of the novel antimicrobial glycollpid caminoside A (1). The structure of caminoside A was elucidated by analysis of spectroscopic data and chemical degradation.
• A MECHANISM FOR THE ANOMERIZATION OF ACETYLATED ALKYL GLYCOPYRANOSIDES
  作者：R. U. Lemieux、W. P. Shyluk

  DOI：10.1139/v55-015

  日期：1955.1.1

  Unequivocal evidence that the anomerization of acetylated alkyl glycopyranosides can proceed by way of an intramolecular mechanism was obtained through the observation that a racemic mixture of methyl β-glucopyranoside tetraacetate with the D-isomer labelled in the methoxyl group with carbon-14 is anomerized both by titanium tetrachloride and boron trifluoride without transfer of radioactive methoxyl

  明确的证据表明乙酰化烷基吡喃糖苷的异构化可以通过分子内机制进行，这是通过观察到 β-吡喃葡萄糖苷四乙酸甲酯与在甲氧基基团中标记的 D-异构体的外消旋混合物与碳 14 异构化而获得的四氯化钛和三氟化硼，而不会将放射性甲氧基转移到 L-异构体上。据认为，这些分子内异构化是最好的合理化结果，因为环境尝试导致糖苷裂解并通过离子对中间体进行，其中阴离子来自苷元基团，但未成功。