p-methoxyphenyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-galactopyranoside | 176165-21-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-galactopyranoside
• 英文别名: Bz(-2)[Bz(-3)][Bn(-6)]Gal(b)-O-Ph(4-OMe)；[(2S,3R,4S,5S,6R)-3-benzoyloxy-5-hydroxy-2-(4-methoxyphenoxy)-6-(phenylmethoxymethyl)oxan-4-yl] benzoate
• CAS: 176165-21-2
• 化学式: C₃₄H₃₂O₉
• 分子量: 584.623
• InChiKey: WVXVBLGROGHKPT-JXJPYGNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-galactopyranoside 在 palladium on activated charcoal 2,3,5-三甲基吡啶 、 氢气 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 8.5h， 生成 p-methoxyphenyl 2,3-di-O-benzoyl-4-O-(α-D-galactopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Double-Chain Bis-Sulfone Neoglycolipids of the 2-, 3-, and 6-Deoxyglobotrioses

  摘要：

  Partially protected 2-(trimethylsilyl)ethyl 2- and 3-deoxyglucosides and 6-deoxylactoside were synthesised via various routes and glycosylated with galabiosyl and galactosyl donors to give the corresponding deoxytrisaccharides. Removal of the protecting groups gave the 2-(trimethylsilyl)ethyl 2-, 3-, and 6-deoxyglobotriosides. Transformation of the protected trisaccharides into trichloroacetimidates, via the corresponding hemiacetals, proceeded in similar to 80% overall yield. Glycosylation of 3-(hexadecylsulfonyl)-2-[(hexadecylsulfonyl)methyl]propanol with the trisaccharidic trichloroacetimidates, in 72-79% yield, followed by removal of protecting groups, gave the title neoglycolipids.

  DOI：

  10.1021/jo951914k
• 作为产物：
  描述：

  4-甲氧基苯基-Β-D-半乳糖苷 在 盐酸 、 4-二甲氨基吡啶 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 吡啶 、 乙腈 为溶剂， 反应 30.0h， 生成 p-methoxyphenyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Double-Chain Bis-Sulfone Neoglycolipids of the 2-, 3-, and 6-Deoxyglobotrioses

  摘要：

  Partially protected 2-(trimethylsilyl)ethyl 2- and 3-deoxyglucosides and 6-deoxylactoside were synthesised via various routes and glycosylated with galabiosyl and galactosyl donors to give the corresponding deoxytrisaccharides. Removal of the protecting groups gave the 2-(trimethylsilyl)ethyl 2-, 3-, and 6-deoxyglobotriosides. Transformation of the protected trisaccharides into trichloroacetimidates, via the corresponding hemiacetals, proceeded in similar to 80% overall yield. Glycosylation of 3-(hexadecylsulfonyl)-2-[(hexadecylsulfonyl)methyl]propanol with the trisaccharidic trichloroacetimidates, in 72-79% yield, followed by removal of protecting groups, gave the title neoglycolipids.

  DOI：

  10.1021/jo951914k

文献信息

• Towards oligosaccharide library synthesis by fluorous mixture method
  作者：Mami Tojino、Mamoru Mizuno

  DOI：10.1016/j.tetlet.2008.07.137

  日期：2008.10

  The synthesis of an oligosaccharide library by a fluorous tag method is reported here. Several acceptors and donors were mixed and glycosylated. The reaction mixture was purified by chromatography over fluorous HPLC to provide disaccharides in order of increasing fluorine content of the tag. This method could be applied to oligosaccharide libraries consisting of two sets of structural isomers.

  此处报道了通过荧光标记法合成寡糖文库。几种受体和供体被混合并被糖基化。将反应混合物通过氟HPLC色谱纯化，以提供二糖，以增加标签的氟含量。该方法可以应用于由两组结构异构体组成的寡糖文库。
• Regioselective Reductive Ring Opening of Benzylidene Acetals Using Triethylsilane and Iodine
  作者：Anup Misra、Rajib Panchadhayee

  DOI：10.1055/s-0029-1219798

  日期：2010.5

  Novel reaction conditions have been developed for the regioselective reductive ring opening of benzylidene acetals in carbohydrate derivatives using triethylsilane and molecular iodine. The reaction is fast, compatible with most of the functional groups encountered in the oligosaccharide synthesis, and yields were excellent. The reaction conditions are equally effective in thioglycosides.

  已经开发了新的反应条件，用于使用三乙基硅烷和分子碘对碳水化合物衍生物中的亚苄基缩醛进行区域选择性还原开环。反应速度快，与寡糖合成中遇到的大多数官能团相容，产率极好。反应条件在硫糖苷中同样有效。
• Synthesis of Double-Chain Bis-Sulfone Neoglycolipids of the 2-, 3-, and 6-Deoxyglobotrioses
  作者：Zhiyuan Zhang、Göran Magnusson

  DOI：10.1021/jo951914k

  日期：1996.1.1

  Partially protected 2-(trimethylsilyl)ethyl 2- and 3-deoxyglucosides and 6-deoxylactoside were synthesised via various routes and glycosylated with galabiosyl and galactosyl donors to give the corresponding deoxytrisaccharides. Removal of the protecting groups gave the 2-(trimethylsilyl)ethyl 2-, 3-, and 6-deoxyglobotriosides. Transformation of the protected trisaccharides into trichloroacetimidates, via the corresponding hemiacetals, proceeded in similar to 80% overall yield. Glycosylation of 3-(hexadecylsulfonyl)-2-[(hexadecylsulfonyl)methyl]propanol with the trisaccharidic trichloroacetimidates, in 72-79% yield, followed by removal of protecting groups, gave the title neoglycolipids.