(+)-menthyl β-D-glucopyranoside | 63268-20-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-menthyl β-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl]oxyoxane-3,4,5-triol
• CAS: 63268-20-2
• 化学式: C₁₆H₃₀O₆
• 分子量: 318.411
• InChiKey: GZSDZJZIZBGBON-FVEFAZKQSA-N

物化性质

• 熔点：
  74-78 °C(Solv: acetone (67-64-1))
• 沸点：
  474.8±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.26
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.38
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (+)-menthyl β-D-glucopyranoside 在 phosphate buffer 、 almond-β-glucosidase 作用下， 反应 24.0h， 生成 D-薄荷醇
  参考文献：
  名称：

  Enantioselective glucosylation of (±)-secondary alcohols with plant glucosyltransferases

  摘要：

  Two glucosyltransferases were isolated from plant cell cultures of Catharanthus roseus and Nicotiana tabacum. The enzyme from C roseus enantioselectively glucosylated (+/-)-secondary alcohols to give the glucosides of (R)-alcohols, while the glucosylation with that from N. tabacum gave preferentially the glucosides of (S)-alcohols. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.022
• 作为产物：
  描述：

  D-薄荷醇 在 三氟化硼乙醚 、 potassium carbonate 、 四甲基胍 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 生成 (+)-menthyl β-D-glucopyranoside
  参考文献：
  名称：

  Enantioselective glucosylation of (±)-secondary alcohols with plant glucosyltransferases

  摘要：

  Two glucosyltransferases were isolated from plant cell cultures of Catharanthus roseus and Nicotiana tabacum. The enzyme from C roseus enantioselectively glucosylated (+/-)-secondary alcohols to give the glucosides of (R)-alcohols, while the glucosylation with that from N. tabacum gave preferentially the glucosides of (S)-alcohols. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.022

文献信息

• Chemical Glucosylation of Labile Natural Products Using a (2-Nitrophenyl)acetyl-Protected Glucosyl Acetimidate Donor
  作者：Julia Weber、Markus Schwarz、Andrea Schiefer、Christian Hametner、Georg Häubl、Johannes Fröhlich、Hannes Mikula

  DOI：10.1002/ejoc.201800260

  日期：2018.6.7

  The synthesis of (2‐nitrophenyl)acetyl (NPAc)‐protected glucosyl donors is described that were designed for the neighboring‐group assisted glucosylation of base‐labile natural products also being sensitive to hydrogenolysis. Glycosylation conditions were optimized using a trichloroacetimidate glucosyl donor, and cyclohexylmethanol and (+)‐menthol as model acceptors. The approach was then extended to

  描述了（2-硝基苯基）乙酰（NPAc）保护的葡萄糖基供体的合成，该供体设计用于邻基辅助的对氢解敏感的碱不稳定天然产物的葡萄糖基化。使用三氯乙酰亚胺葡萄糖基供体、环己基甲醇和 (+)-薄荷醇作为模型受体优化糖基化条件。然后将该方法扩展到用于合成 1,2-反式糖苷的单锅法。该方法最终用于改进掩蔽真菌毒素 T2-O-β,d-葡萄糖苷的合成。
• Neuberg et al., Fermentforschung, 1929, vol. 10, p. 491,515, 516, 520
  作者：Neuberg et al.

  DOI：——

  日期：——
• Treibs; Franke, Justus Liebigs Annalen der Chemie, 1950, vol. 570, p. 76,80, 85
  作者：Treibs、Franke

  DOI：——

  日期：——