3,4,6-tri-O-benzyl-α-D-galactopyranose | 114179-79-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-benzyl-α-D-galactopyranose
• 英文别名: 3,4,6-tri-O-benzyl-D-galactopyranose；3,4,6-tris-O-benzyl-D-galactopyranose；(2S,3R,4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane-2,3-diol
• CAS: 114179-79-2
• 化学式: C₂₇H₃₀O₆
• 分子量: 450.532
• InChiKey: IAEIBZGLRQJURL-SEFGFODJSA-N

物化性质

• 沸点：
  604.3±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4,6-三-O-乙酰基-Alpha-D-吡喃半乳糖-1,2-(甲基原乙酸酯) 在 氢氧化钾 、 硫酸 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 4.5h， 生成 3,4,6-tri-O-benzyl-α-D-galactopyranose
  参考文献：
  名称：

  Sex Pheromones of the Hair Crab Erimacrus isenbeckii. II. Synthesis of Ceramides

  摘要：

  To confirm their structures and to assess the pheromonal activity, novel ceramides, possible sex pheromones of the hair crab Erimacrus isenbeckii, were synthesized from D-galactose. The synthetic ceramides were identical with the natural ceramides.

  DOI：

  10.1021/np010177m

文献信息

• Protecting carbohydrates with ethers, acetals and orthoesters under basic conditions
  作者：Yang Liang、Christian M. Pedersen

  DOI：10.1039/d1ob01467f

  日期：——

  Chlorinated ethyl and vinyl ethers are introduced at various positions of carbohydrates. Depending on the relative stereochemistry, vinylethers, acetals or orthoesters are formed under basic conditions. The products are stable, but are easily deprotected after dechlorination. The scope of the intramolecular protection is studied using common pentoses and hexoses.

  在碳水化合物的不同位置引入氯化乙基醚和乙烯基醚。取决于相对立体化学，乙烯基醚、缩醛或原酸酯在碱性条件下形成。产品稳定，但脱氯后易脱保护。使用常见的戊糖和己糖研究分子内保护的范围。
• Regio- and Stereoselective Synthesis of 1,2-<i>cis</i>-Glycosides by Anomeric <i>O</i>-Alkylation with Organoboron Catalysis
  作者：Sanae Izumi、Yusuke Kobayashi、Yoshiji Takemoto

  DOI：10.1021/acs.orglett.8b03823

  日期：2019.2.1

  Regio- and stereoselective synthesis of 1,2-cis-glycosides has been achieved by catalytic anomeric O-alkylation using organoboron compounds. Modulating steric and electronic factors of both catalysts and substrates enables activation of the axially oriented anomeric oxygens of glucose-derived dialkoxyborates. The mild reaction conditions allow broad functional-group tolerance. This approach can be

  通过使用有机硼化合物的催化异头O-烷基化已经实现了1，2-顺式糖苷的区域和立体选择性合成。调节催化剂和底物两者的空间和电子因子使得能够活化葡萄糖衍生的二烷氧基硼酸盐的轴向取向的异头氧。温和的反应条件允许宽泛的官能团耐受性。该方法可以应用于寡糖的有效顺序合成。
• Ionic liquids as phase transfer catalysts: Enhancing the biphasic extractive epoxidation reaction for the selective synthesis of β-O-glycosides
  作者：Cintia C. Santiago、Leticia Lafuente、Rodolfo Bravo、Gisela Díaz、Agustín Ponzinibbio

  DOI：10.1016/j.tetlet.2017.08.033

  日期：2017.9

  Ionic liquids promoted the direct epoxidation of glycals acting as PTC. 1,2-anhydrosugars were prepared by the oxidation of glycals under biphasic conditions with dimethydioxirane generated in situ from oxone/acetone and amphiphilic IL’s as catalysts. β-O-glycosides were synthesized in good yields by the nucleophilic ring opening of epoxy carbohydrate derivatives. Also, 3,4,6-benzyl protected carbohydrates

  离子液体促进了充当PTC的糖基的直接环氧化。通过在两相条件下用二氧环乙烷/丙酮和两亲性IL's原位生成的二甲基二环氧乙烷氧化糖类来制备1,2-脱水糖。通过环氧碳水化合物衍生物的亲核开环，可以高收率合成β-O-糖苷。同样，可以通过该方法制备3,4,6-苄基保护的碳水化合物和β-N-糖苷。