(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-(3-phenylprop-2-enoxy)oxane-3,4,5-triol | 34047-83-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-(3-phenylprop-2-enoxy)oxane-3,4,5-triol
• CAS: 34047-83-1
• 化学式: C₁₅H₂₀O₆
• 分子量: 296.32
• InChiKey: KHPCPRHQVVSZAH-GZBLMMOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-(3-phenylprop-2-enoxy)oxane-3,4,5-triol 、 苯甲醛二甲缩醛 在 camphor-10-sulfonic acid 、 三乙胺 作用下， 以 乙腈 为溶剂， 以92%的产率得到(E)-3-phenyl-2-propenyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Alkenyl β-d-galactopyranoside derivatives as efficient chiral templates in stereoselective cyclopropanation and epoxidation reactions

  摘要：

  The synthesis of a wide range of alkenyl 4,6-O-(S)-benzylidene-beta-D-galactopyranosides is described. The cyclopropanation and epoxidation reactions of these compounds were developed. Cyclopropanation reactions took place with high stereoselectivity giving diastereomeric excesses of up to 100%. As a part Of Our aim in studying hydroxyl-directed reactions, their epoxidation with m-CPBA was carried out High diastereomeric excesses (80-100%) were obtained when the hydroxyl group at C-2 of the auxiliary was unprotected The beta-D-galactopyranoside moiety constitutes as an interesting auxiliary, due to its efficient chirality transfer capability as well as providing a way to obtain a variety of glycolipid derivatives (c) 2009 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.003
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-(3-phenylprop-2-enoxy)oxane-3,4,5-triol
  参考文献：
  名称：

  Alkenyl β-d-galactopyranoside derivatives as efficient chiral templates in stereoselective cyclopropanation and epoxidation reactions

  摘要：

  The synthesis of a wide range of alkenyl 4,6-O-(S)-benzylidene-beta-D-galactopyranosides is described. The cyclopropanation and epoxidation reactions of these compounds were developed. Cyclopropanation reactions took place with high stereoselectivity giving diastereomeric excesses of up to 100%. As a part Of Our aim in studying hydroxyl-directed reactions, their epoxidation with m-CPBA was carried out High diastereomeric excesses (80-100%) were obtained when the hydroxyl group at C-2 of the auxiliary was unprotected The beta-D-galactopyranoside moiety constitutes as an interesting auxiliary, due to its efficient chirality transfer capability as well as providing a way to obtain a variety of glycolipid derivatives (c) 2009 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.003

文献信息

• A novel strategy to improve the aromatic alcohols tolerance of enzyme for preparative-scale synthesis of natural glycosides
  作者：Youzhi Zhou、Lu Zhao、Ke Liu、Jinsong Zhang、Jianlin Chu、Bingfang He

  DOI：10.1016/j.catcom.2017.07.025

  日期：2017.12

  Aromatic alcohols are liable to result in enzyme inactivation. A novel strategy was established for improving the aromatic alcohol tolerance of β-galactosidase (BMG) from Bacillus megaterium YZ08. The half-life of BMG in 200 mM vanillyl alcohol solution was dramatically increased by 9–123 times with the addition of hydrophilic solvents. In 30% DMSO, the reaction concentration of aromatic alcohol could

  芳香醇容易导致酶失活。建立了改善巨大芽孢杆菌YZ08的β-半乳糖苷酶（BMG）芳香醇耐受性的新策略。添加亲水性溶剂后，BMG在200 mM香草醇溶液中的半衰期显着增加了9–123倍。在30％DMSO中，芳香醇的反应浓度可达到300–400 mM，并以100 mL的比例成功获得0.85–2.44 g的天然糖苷。这种简单有效的策略在处理酶反应的制备规模开发时显示出潜在的应用。