4-methoxyphenyl 4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside | 1104513-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside
• 英文别名: p-methoxyphenyl 4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside；4-methoxyphenyl 4-O-acetyl-2,6-di-O-benzyl-beta-d-galactopyranoside；[(2R,3R,4S,5R,6S)-4-hydroxy-6-(4-methoxyphenoxy)-5-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 1104513-35-0
• 化学式: C₂₉H₃₂O₈
• 分子量: 508.568
• InChiKey: NIJIWGSLBKOKDI-JYJZCUDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside 在 三乙基硅烷 、 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 p-methoxyphenyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-glucopyranosyl-(1 → 3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Chemical synthesis of a tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1

  摘要：

  Chemical synthesis of the tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1 is reported. The stereoselective glycosylations were achieved by activation of the thioglycoside donors using N-iodosuccinimide in the presence of La(OTf)(3) varying temperature per the need of 1,2-cis or 1,2-trans glycosylations. The target tetrasaccharide is reported in the form of its p-methoxyphenyl glycoside that can be cleaved selectively from the per-O-acetylated derivative allowing further glycoconjugate formation using trichloroacetimidate chemistry. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.05.018
• 作为产物：
  描述：

  4-甲氧苯基2,6-二-O-苄基-3,4-O-异亚丙基-β-D-吡喃半乳糖苷 在 camphor-10-sulfonic acid 、 溶剂黄146 作用下， 以 水 、 乙腈 为溶剂， 反应 2.5h， 生成 4-methoxyphenyl 4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Chemical synthesis of a tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1

  摘要：

  Chemical synthesis of the tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1 is reported. The stereoselective glycosylations were achieved by activation of the thioglycoside donors using N-iodosuccinimide in the presence of La(OTf)(3) varying temperature per the need of 1,2-cis or 1,2-trans glycosylations. The target tetrasaccharide is reported in the form of its p-methoxyphenyl glycoside that can be cleaved selectively from the per-O-acetylated derivative allowing further glycoconjugate formation using trichloroacetimidate chemistry. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.05.018

文献信息

• Efficient acylation and sulfation of carbohydrates using sulfamic acid, a mild, eco-friendly catalyst under organic solvent-free conditions
  作者：Abhishek Santra、Goutam Guchhait、Anup Kumar Misra

  DOI：10.1039/c1gc15122c

  日期：——

  fast and efficient acylation of carbohydrate derivatives and free sugars using a stoichiometric quantity of acylating agents in the presence of sulfamic acid, an environmentally benign catalyst, under organic solvent-free conditions is reported. Excellent yields in the selective acylation and sulfation of carbohydrate derivatives have also been achieved using sulfamic acid as the catalyst. The reaction

  快速高效 酰化 的 碳水化合物衍生物 在存在以下条件下，使用化学计量的酰化剂制备游离糖和游离糖 氨基磺酸，对环境无害 催化剂，在有机 溶剂-无条件的报道。选择性的酰化和硫酸化硫酸具有优异的收率碳水化合物衍生物 也已经通过使用 氨基磺酸 作为 催化剂。反应速度快，收率优异。
• La(OTf)3: An Efficient Promoter for Thioglycoside Activation in Conjunction with N-Iodosuccinimide
  作者：Balaram Mukhopadhyay、Somnath Mukherjee

  DOI：10.1055/s-0030-1259016

  日期：2010.12

  Use of La(OTf)3 as a Lewis acid promoter for N-iodosuccinimide-mediated activation of thioglycosides is reported. The glycosylation reactions proceeded smoothly with good to excellent yields and stereoselectivity.

  使用La(OTf)3作为路易斯酸促使剂，报告了N-碘代琥珀酰亚胺介导的硫糖苷活化。糖苷化反应顺利进行，产率良好至优异，立体选择性也很好。
• Regioselective Acylation of Diols and Triols: The Cyanide Effect
  作者：Peng Peng、Michael Linseis、Rainer F. Winter、Richard R. Schmidt

  DOI：10.1021/jacs.6b02454

  日期：2016.5.11

  positioned hydroxy groups. As cyanide is capable of various kinds of hydrogen bonding and as it is a quite strong sterically nondemanding base, regioselective O-acylations should be possible at low temperatures even at sterically congested positions, thus permitting formation and also isolation of the kinetic product. Indeed, 1,2-cis-diols, having an equatorial and an axial hydroxy group, benzoyl cyanide

  碳水化合物化学的中心主题包括碳水化合物的结构修饰和寡糖合成。两者都需要受区域选择性保护的构建块，这些构建块主要通过间接多步程序获得。因此，需要针对特定​​羟基的直接保护方法。双氢键最终将区分不同位置的羟基。由于氰化物能够形成各种氢键，并且它是一种非常强的空间要求不高的碱，因此即使在空间拥挤的位置，也应该可以在低温下进行区域选择性 O-酰化，从而允许形成和分离动力学产物。实际上，具有赤道和轴羟基的 1,2-顺式二醇、苯甲酰氰或乙酰氰作为酰化剂，和 DMAP 作为催化剂在 -78°C 下产率热力学上不利的轴向 O-酰化产物；在这些条件下未观察到酰基迁移。这种现象被 3,4-O-未保护的半乳糖和吡喃岩藻糖苷以及 2,3-O-未保护的吡喃甘露糖苷证实。即使对于作为三醇的 3,4,6-O-未保护的吡喃半乳糖苷，轴向 4-O-酰化也明显快于伯 6-羟基的 O-酰化。氢键对这种不寻常的区域选择性的重要性可以通过
• Chemical synthesis of the hexasaccharide related to the repeating unit of the capsular polysaccharide from carbapenem resistant Klebsiella pneumoniae 2796 and 3264
  作者：Vikramjit Sarkar、Balaram Mukhopadhyay

  DOI：10.1039/c6ra07351d

  日期：——

  The total synthesis of the hexasaccharide repeating unit of the CPS from carbapenem resistant K. pneumoniae 2796 and 3264 is reported using a sequential glycosylations approach. The total synthesis has been accomplished by glycosylation of rationally protected monosaccharide synthons derived from the commercially available sugars. The required uronic acid on the galactose moiety was successfully installed

  使用顺序糖基化方法报道了来自碳青霉烯抗性肺炎克雷伯氏菌2796和3264的CPS六糖重复单元的总合成。总合成已经通过对衍生自市售糖的合理保护的单糖合成子进行糖基化来完成。通过TEMPO介导的后期氧化，成功地在半乳糖部分上安装了所需的尿酸。使用H 2 SO 4-二氧化硅作为促进剂，通过NIS介导的硫糖苷的活化进行糖基化。氯乙酸基团被广泛用作临时保护基团，以促进立体选择性糖基化。
• Chemical synthesis of the tetrasaccharide repeating unit of the O-polysaccharide isolated from Azospirillum brasilense SR80
  作者：Vikramjit Sarkar、Balaram Mukhopadhyay

  DOI：10.1016/j.carres.2015.01.008

  日期：2015.4

  A linear strategy has been developed for the synthesis of the tetrasaccharide repeating unit of the O-polysaccharide from Azospirillum brasilense SR80. Stepwise glycosylation of the rationally protected thioglycoside donors activated by NIS in the presence of La(OTf)(3) furnished the target tetrasaccharide. The glycosylation reactions resulted in the formation of the desired linkage with absolute stereo-selectivity and afforded the required derivatives in good to excellent yields. The phthalimido group has been used as the precursor of the desired acetamido group to meet the requirement of 1,2-trans glycosidic linkage. (C) 2015 Elsevier Ltd. All rights reserved.