4-methoxyphenyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranoside | 343254-39-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranoside
• 英文别名: 4-methoxyphenyl 2,4,6-O-tri-O-acetyl-3-O-allyl-β-D-galactopyranoside；p-methoxyphenyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranoside；[(2R,3S,4S,5R,6S)-3,5-diacetyloxy-6-(4-methoxyphenoxy)-4-prop-2-enoxyoxan-2-yl]methyl acetate
• CAS: 343254-39-7
• 化学式: C₂₂H₂₈O₁₀
• 分子量: 452.458
• InChiKey: MAGSUXKTAQBPOM-CDJZJNNCSA-N

物化性质

• 沸点：
  542.3±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranoside 在 吡啶 、 甲醇 、 ammonium cerium(IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 camphor-10-sulfonic acid 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 11.5h， 生成 4-methoxyphenyl O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside
  参考文献：
  名称：

  Synthetic Approach Toward the Partial Sequences of Betaglycan in the Linkage Region on Solid Support and in Solution Phase

  摘要：

  We have synthesized, for the first time, the partial sequence of the betaglycan composed of the tetraosyl hexapeptide, which was directly usable as a probe for enzymatic glycosyl transfer. Stepwise elongation afforded the corresponding tetraosyl trichloroacetimidate. The common glycosyl dipeptide:[beta-D-GlcA-(1 -> 3)-beta-D-Gal-(1 -> 3)-beta-D-Gal-(1 -> 4)-beta-D- Xyl-(1 -> O)-Ser-Gly] was synthesized by glycosylation of the corresponding tetraosyl trichloroacetimidate and Ser-Gly moiety. The glycosyl dipeptide was coupled with other core peptide parts in solution phase and on a solid support. These glycosyl hexapeptides were then transformed into the desired target compounds.

  DOI：

  10.1080/07328300701296810
• 作为产物：
  描述：

  4-甲氧基苯基-Β-D-半乳糖苷 在 吡啶 、 二正丁基氧化锡 作用下， 以 甲苯 为溶剂， 反应 22.0h， 生成 4-methoxyphenyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranoside
  参考文献：
  名称：

  2，6-二取代的2- O-苯甲酰基在糖基化反应中的相邻基团参与：机理研究

  摘要：

  对于NIS / TfOH介导的4-甲氧基苯基2,4,6-四-O-乙酰基-β-D-吡喃半乳糖苷和带有乙酰基，苯甲酰基，2,6-二甲氧基苯甲酰基的硫代半乳糖苷的反应，获得了不同的收率和糖基化立体选择性。在2-位的是2,4,6-三甲基苯甲酰基或2,6-二氯苯甲酰基，其余为乙酰基。4-甲基苯基2,3,4,6-四的X射线结构Ö - （2,4,6-三甲基苯甲酰）-1-硫代β-d-galactopyr anoside和4-甲基苯基3,4- ø -异亚丙基-2,6-二-O-（2,4,6-三甲基苯甲酰基）-1-硫代-β-D-吡喃半乳糖苷显示轻微扭曲的4 C 1椅子构象。可变温度NMR显示4-甲基苯基2,3,4,6-tetra- O的活化-（2,4,6-三甲基苯甲酰基）-1-硫代-β-D-吡喃半乳糖苷仅提供二恶唑鎓离子，而4-甲基苯基3,4,6-三-O-乙酰基-2- O-（2,4， 6-三甲基苯甲酰基）-1-

  DOI：

  10.1080/07328303.2010.508141

文献信息

• Remarkable Solvent Effect on Pd(0)-Catalyzed Deprotection of Allyl Ethers Using Barbituric Acid Derivatives: Application to Selective and Successive Removal of Allyl, Methallyl, and Prenyl Ethers
  作者：Hirokazu Tsukamoto、Takamichi Suzuki、Yoshinori Kondo

  DOI：10.1055/s-2007-992352

  日期：——

  Pd(0)-catalyzed deprotection of allyl ethers using barbituric acid derivatives in protic polar solvent such as MeOH and aqueous 1,4-dioxane proceeds at room temperature without affecting a wide variety of functional groups. Control of the reaction temperature allows selective and successive cleavage of allyl, methallyl, and prenyl ethers. A study of ligand effects on the deprotection reveals that the

  使用巴比妥酸衍生物在质子极性溶剂（如 MeOH 和 1,4-二恶烷水溶液中）中 Pd(0) 催化的烯丙基醚脱保护在室温下进行，而不会影响多种官能团。反应温度的控制允许烯丙基、甲代烯丙基和异戊二烯醚的选择性和连续裂解。配体对脱保护作用的研究表明，甲醇中反应性的提高是由于加速氧化加成到 Pd(0)。
• Selective acetolysis of primary benzyl groups in carbohydrate derivatives under the mild reaction condition
  作者：Monalisa Kundu、Anup Kumar Misra

  DOI：10.1016/j.carres.2019.107830

  日期：2019.12

  in a wide variety of carbohydrate derivatives was achieved in excellent yield using acetic anhydride and perchloric acid supported over silica (HClO4-SiO2) as a solid acid catalyst in a fast reaction condition without using any organic solvent. The reaction condition is significantly rapid and can be scaled up for its use in the multi-step oligosaccharide synthesis.

  在快速反应条件下，使用乙酸酐和高氯酸负载在二氧化硅（HClO4-SiO2）上作为固体酸催化剂，无需使用任何有机溶剂，即可以优异的产率实现多种碳水化合物衍生物中伯苄氧基的选择性乙酰化。反应条件非常迅速，可以扩大规模以用于多步寡糖合成中。
• Synthesis of Phosphorylated and Sulfated Glycosyl Serines in the Linkage Region of the Glycosaminoglycans
  作者：Jun-ichi Tamura、Junko Nishihara

  DOI：10.1021/jo001540h

  日期：2001.5.1

  We synthesized novel acidic glycans having acidic groups located in the linkage region of the glycosaminoglcans (GAGs). The targeted compounds, beta -D-Xyl(2P)-Ser (1), beta -D-Gal(+/- 6S)-(1 -->4)-beta- D-Xyl(2P)-Ser (3 and 2), beta -D-Gal(+/- 6S)-(1 -->3)-beta -D-Gal-(1 -->4)-beta -D-Xyl(2P)-Ser (5 and 4), and beta -D-Gal- (1 -->3)-beta -D-Gal(6S)-(1 -->4)-beta -D-Xyl(2P)-Ser (6) contain phosphate and/or sulfate at the specified positions. Some of them (3,5, and 6) are the first synthesized examples of natural-type glycoconjugates that simultaneously possess phosphate and sulfate as well as carboxylic acid.