N-{(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[8-(4-methoxy-phenoxy)-octyloxy]-tetrahydro-pyran-3-yl}-acetamide | 178420-48-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-{(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[8-(4-methoxy-phenoxy)-octyloxy]-tetrahydro-pyran-3-yl}-acetamide
• 英文别名: 8-(p-methoxyphenoxy)-octyl 2-deoxy 2-acetamido β-D-glucopyranoside
• CAS: 178420-48-9
• 化学式: C₂₃H₃₇NO₈
• 分子量: 455.549
• InChiKey: CZOVSZHXVRAGLM-GNJRFXKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  32.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  126.71
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-{(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[8-(4-methoxy-phenoxy)-octyloxy]-tetrahydro-pyran-3-yl}-acetamide 在 甲醇 、 calcium sulfate 、 sodium methylate 、 氰化汞 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 硝基甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 18.0h， 生成 N-[(2R,3R,4R,5S,6R)-5-Hydroxy-6-hydroxymethyl-2-[8-(4-methoxy-phenoxy)-octyloxy]-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Towards oligosaccharide libraries: A study of the random galactosylation of unprotected N-acetylglucosamine

  摘要：

  A single reaction of an unprotected beta-D-GlcNAc glycoside with tetra-O-acetyl-alpha-D-galactopyranosyl trichloroacetimidate in dioxane, catalyzed by BF3-etherate, was shown to yield all six possible Gal-GlcNAc disaccharides. This result is surprising not only because significant amounts of alpha-linked disaccharides were formed, despite the presence of a participating group at O-2 of the glycosyl donor, but also because glycosylation of the primary OH-6 is not the dominant reaction. These results suggest 'random-glycosylation' to be a valid strategy for the rapid production of oligosaccharide libraries. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0968-0896(96)00064-8
• 作为产物：
  描述：

  8-p-methoxyphenoxyloctanol 在 甲醇 、 calcium sulfate 、 sodium methylate 、 氰化汞 作用下， 反应 25.0h， 生成 N-{(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[8-(4-methoxy-phenoxy)-octyloxy]-tetrahydro-pyran-3-yl}-acetamide
  参考文献：
  名称：

  Towards oligosaccharide libraries: A study of the random galactosylation of unprotected N-acetylglucosamine

  摘要：

  A single reaction of an unprotected beta-D-GlcNAc glycoside with tetra-O-acetyl-alpha-D-galactopyranosyl trichloroacetimidate in dioxane, catalyzed by BF3-etherate, was shown to yield all six possible Gal-GlcNAc disaccharides. This result is surprising not only because significant amounts of alpha-linked disaccharides were formed, despite the presence of a participating group at O-2 of the glycosyl donor, but also because glycosylation of the primary OH-6 is not the dominant reaction. These results suggest 'random-glycosylation' to be a valid strategy for the rapid production of oligosaccharide libraries. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0968-0896(96)00064-8

文献信息

• Generation of β-Linked GlcNac and GalNAc Terminating Disaccharide Library through Glycosylation on Unprotected Monosaccharides
  作者：Yili Ding、Chamakura V.N.S. Vara Prasad、Bingyun Wang

  DOI：10.2174/1570178614666170728152602

  日期：2018.6.13

  Background: The GlcNAc related sulfated disaccharides were reported to show inhibitory activity on breast tumor cells (MDA-MB-231). However, synthesis of sulfated disaccharides is laborious and time consuming, and there is a need to find more efficient methods to generate the sulfated disaccharide libraries in acceptable ratios and in respectable yields. Random glycosylation followed by sulfation may be a good method to synthesize sulfated disaccharide library. However, there is a dearth of simple methods to generate the GalNAc and GlcNAc related disaccharides with acceptable ratio by random glycosylation. Results: Following a generic procedure, random glycosylation of unprotected monosaccharides and followed by deprotection, acetylation, deacetylation, and purification, yielded the GalNAc-GlcNAc disaccharide library containing three β-linked disaccharides with a 1:1:1 ratio and the GlcNAc-Gal disaccharide library containing four β-linked disaccharides with 1:1:2:2 ratio. These results were confirmed by comparison of their proton NMR spectra with that of standard disaccharides. Conclusion: Random glycosylation was employed to generate GalNAc and GlcNAc related disaccharide libraries and was demonstrated as the most efficient method thus far for the synthesis of GalNAc and GlcNAc related disaccharide libraries with excellent ratios, which further can be used as the starting materials for random sulfation to synthesize the sulfated disaccharide libraries.

  背景：据报道，与 GlcNAc 相关的硫酸化二糖对乳腺肿瘤细胞（MDA-MB-231）具有抑制活性。然而，硫酸化二糖的合成费时费力，因此需要找到更有效的方法，以可接受的比例和可观的产量生成硫酸化二糖文库。随机糖基化后硫酸化可能是合成硫酸化二糖文库的好方法。然而，通过随机糖基化以可接受的比例生成 GalNAc 和 GlcNAc 相关二糖的简单方法还很缺乏。 结果：按照一般的程序，对未受保护的单糖进行随机糖基化，然后进行去保护、乙酰化、去乙酰化和纯化，得到了含有三种β连接二糖的GalNAc-GlcNAc二糖文库，其比例为1:1:1；含有四种β连接二糖的GlcNAc-Gal二糖文库，其比例为1:1:2:2。结论：随机糖基化被用来生成 GalNAc 和 GlcNAc 相关二糖文库，并被证明是迄今为止合成 GalNAc 和 GlcNAc 相关二糖文库的最有效方法，其比例极佳，可进一步用作随机硫酸化合成硫酸化二糖文库的起始材料。