allyl 2,3,4,6-tetra-O-benzyl-D-galactopyranoside | 214490-83-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,4,6-tetra-O-benzyl-D-galactopyranoside
• 英文别名: α,β-allyloxy-2,3,4,6-tetra-O-benzyl-d-galactose；(2R,3S,4S,5R)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-enoxyoxane
• CAS: 214490-83-2
• 化学式: C₃₇H₄₀O₆
• 分子量: 580.721
• InChiKey: LFXIXGYQTQLJCK-HRKBRENZSA-N

物化性质

• 沸点：
  679.3±55.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 2,3,4,6-tetra-O-benzyl-D-galactopyranoside 在 盐酸 、 palladium 10% on activated carbon 、 potassium tert-butylate 、 氨 、 氢气 、 caesium carbonate 、 戴斯-马丁氧化剂 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.08h， 生成 2-O-octyl-3,5-dihydroxy-6-methylpyridine
  参考文献：
  名称：

  An unusual synthesis of 2-pyridone and 3,5-dihydroxypyridine from a carbohydrate

  摘要：

  An unusual aromatization to perbenzylated 3,5-dihydroxy-6-(hydroxymethyl)-2-pyridone was demonstrated utilizing sugar lactam, under strong basic conditions, derived from D-Galactose. 2-Pyridone was efficiently converted into a pharmaceutically relevant structure 3,5-dihydroxy pyridine salt to demonstrate its synthetic utility. This result is the first report for 2-pyridone synthesis from a carbohydrate, and also first of its kind for a novel 3,5-dihydroxypyridine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.083
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 13.5h， 生成 allyl 2,3,4,6-tetra-O-benzyl-D-galactopyranoside
  参考文献：
  名称：

  An unusual synthesis of 2-pyridone and 3,5-dihydroxypyridine from a carbohydrate

  摘要：

  An unusual aromatization to perbenzylated 3,5-dihydroxy-6-(hydroxymethyl)-2-pyridone was demonstrated utilizing sugar lactam, under strong basic conditions, derived from D-Galactose. 2-Pyridone was efficiently converted into a pharmaceutically relevant structure 3,5-dihydroxy pyridine salt to demonstrate its synthetic utility. This result is the first report for 2-pyridone synthesis from a carbohydrate, and also first of its kind for a novel 3,5-dihydroxypyridine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.083

文献信息

• Fluorine-Directed β-Galactosylation: Chemical Glycosylation Development by Molecular Editing
  作者：Estelle Durantie、Christoph Bucher、Ryan Gilmour

  DOI：10.1002/chem.201200468

  日期：2012.6.25

  Validation of the 2‐fluoro substituent as an inert steering group to control chemical glycosylation is presented. A molecular editing study has revealed that the exceptional levels of diastereocontrol in glycosylation processes by using 2‐fluoro‐3,4,6‐tri‐O‐benzyl glucopyranosyl trichloroacetimidate (TCA) scaffolds are a consequence of the 2R,3S,4S stereotriad. This study has also revealed that epimerization

  提出了将2-氟取代基作为控制化学糖基化反应的惰性指导基团的验证方法。一项分子编辑研究表明，通过使用2-氟-3,4,6-三-O-苄基吡喃葡萄糖基三氯乙酰亚氨酸酯（TCA）支架，糖基化过程中非对映异构控制的异常水平是2 R，3 S，4的结果S立体三合会。这项研究还表明，C4的差向异构作用会导致β选择性大大提高（高达β/α300：1）。
• Gold(III)-Catalyzed Glycosylation using Phenylpropiolate Glycosides: Phenylpropiolic Acid, An Easily Separable and Reusable Leaving Group
  作者：Mukta Shaw、Rima Thakur、Amit Kumar

  DOI：10.1021/acs.joc.8b02422

  日期：2019.1.18

  synthesized benchtop stable phenylpropiolate glycosyl (PPG) donors. Gold(III)-catalyzed activation of PPGs proceeds well with various carbohydrate and noncarbohydrate-based glycosyl acceptors and leads to their corresponding O/N-glycosides in good to excellent yields with regeneration of reusable and easily separable phenylpropiolic acid. Differentially protected PPGs reacted well under the optimized reaction

  使用新合成的台式稳定苯丙酸苯丙酯糖基（PPG）供体，开发了一种有效且操作简单的金（III）催化的糖基化方案。金（III）催化的PPG活化与各种基于碳水化合物和非碳水化合物的糖基受体进行得很好，并导致其相应的O / N-糖苷的收率好至极好，并具有可重复使用和易于分离的苯丙酸的再生。差异保护的PPG在优化的反应条件下反应良好。特别地，在甘露糖基和鼠李糖基PPG供体上观察到良好的异头选择性。初步的机理研究表明，与酯基相邻的三键的存在对于激活至关重要，并且基于PPG的供体显示出比类似的乙酸和苯甲酸酯供体更高的反应性。
• Direct <i>C</i>-Glycosylation of Organotrifluoroborates with Glycosyl Fluorides and Its Application to the Total Synthesis of (+)-Varitriol
  作者：Jing Zeng、Seenuvasan Vedachalam、Shaohua Xiang、Xue-Wei Liu

  DOI：10.1021/ol102473k

  日期：2011.1.7

  C-glycosides via BF3·Et2O promoted coupling of organotrifluoroborates and glycosyl fluorides is reported. The application of this method was further demonstrated by the concise and efficient total synthesis of (+)-varitriol in only seven steps.

  据报道，通过BF 3 ·Et 2 O促进了有机三氟硼酸酯和糖基氟化物的偶联，采用了温和，立体选择性和快速的方法访问炔基和烯基C-糖苷。该方法的应用通过仅七个步骤的简明有效的全合成（+）-varitriol进一步得到了证明。
• Synthesis of the hyper-branched core tetrasaccharide motif of chloroviruses
  作者：Bijoyananda Mishra、Sujit Manmode、Gulab Walke、Saptashwa Chakraborty、Mahesh Neralkar、Srinivas Hotha

  DOI：10.1039/d0ob02176h

  日期：——

  residues in which L-fucose is connected to D-xylose and L-rhamnose via a 1,2-trans glycosidic bond, whereas with the D-galactose residue is connected through a 1,2-cis glycosidic bond. A thorough and comprehensive study of various accountable factors enabled us to install a 1,2-cis galactopyranosidic linkage in a stereoselective fashion under [Au]/[Ag]-catalyzed glycosidation conditions en route to the

  复杂寡糖的化学合成，特别是具有一个或多个1,2-顺式糖苷键的超支化结构的寡糖，是一项艰巨的任务。糖基供体和受体的互补反应性，以及溶剂/温度/活化剂的适当调节，以及空间拥挤的糖基受体的糖基化收率降低，是使这种合成令人望而生畏的几个因素。在本文中，我们报道了与人和小鼠模型中与认知功能降低相关的氯病毒的半保守超支化核心四糖基序的合成。目标四糖包含四个不同的糖残基，其中L-岩藻糖与D-木糖和L-鼠李糖通过1，2-反式糖苷键，而与D-半乳糖残基通过1，2-顺式糖苷键连接。各责任因素进行全面，综合的研究使我们能够安装1,2-顺galactopyranosidic联动的立体方式下的[金] / [公司]催化的糖苷化条件途中到14步的目标四糖主题。