1,2:3,4-di-O-isopropylidene-6-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-galactopyranose | 62043-20-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:3,4-di-O-isopropylidene-6-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-galactopyranose
• 英文别名: [(2S,3S,4R,5R,6R)-4,5-diacetyloxy-2-methyl-6-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-3-yl] acetate
• CAS: 62043-20-3
• 化学式: C₂₄H₃₆O₁₃
• 分子量: 532.542
• InChiKey: WRVXVCUEYPMFMV-VEEVAJAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1,2:3,4-di-O-isopropylidene-6-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-galactopyranose 在 三氟乙酸 、 sodium methylate 作用下， 以 水 、 甲醇 为溶剂， 反应 1.25h， 生成 6-O-(α-L-rhamnopyranosyl)-α-D-galactopyranose 、 6-O-(α-L-rhamnopyranosyl)-β-D-galactopyranose
  参考文献：
  名称：

  Synthesis of fluorescently labelled rhamnosides: probes for the evaluation of rhamnogalacturonan II biosynthetic enzymes

  摘要：

  Three fluorescently labelled saccharides 10-12, representing structures found in pectic glycan rhamnogalacturonan II (RG-II), were synthesised by chemical glycosylation of O-6 of diacetone-D-galactose followed by deprotection and reductive amination with amino-substituted fluorophore APTS. This convenient method installs a common aminogalactitol-based tether in order to preserve the integrity of the reducing end of specific carbohydrates of interest. APTS-labelled glycans prepared in this manner were purified by carbohydrate gel electrophoresis and subjected to capillary electrophoresis analysis, as a basis for the subsequent development of high sensitivity assays for RG-II-active enzymes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.03.039
• 作为产物：
  描述：

  乙基 2,3,4-三-O-乙酰基-6-脱氧-1-硫代-alpha-L-吡喃甘露糖苷 在 4 A molecular sieve 、 copper(II) bis(trifluoromethanesulfonate) 、 甲基三辛基氯化铵 、 copper(II) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 1,2:3,4-di-O-isopropylidene-6-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-galactopyranose
  参考文献：
  名称：

  异头磺酰亚胺的合成及其作为新的糖基供体家族的用途

  摘要：

  我们介绍了一种方便的异头磺酰亚胺合成方法，其作为糖基供体的能力已经用各种亲硫试剂和受体进行了测试。

  DOI：

  10.1002/1099-0690(20021)2002:1<171::aid-ejoc171>3.0.co;2-7

文献信息

• Amberlyst 15 as a mild and effective activator for the glycosylation with disarmed glycosyl trichloroacetimidate donors
  作者：Qiang Tian、Shuo Zhang、Qian Yu、Mei-Bo He、Jin-Song Yang

  DOI：10.1016/j.tet.2006.12.091

  日期：2007.3

  Amberlyst 15 acidic resin has been shown to be a mild and effective activator for the glycosylation with commonly used disarmed glycosyl trichloroacetimidate donors. Glucosylation, galactosylation, rhamnosylation, and lactosylation of a panel of representative alcohol and thiol acceptors promoted by Amberlyst 15 allowed for the formation of structurally diverse O- or S-linked oligosaccharides and glycosylated

  Amberlyst 15酸性树脂已被证明是一种温和有效的活化剂，可用于与常用的脱甲糖基三氯乙酰亚氨酸酯供体进行糖基化反应。由Amberlyst 15促进的一组代表性醇和硫醇受体的糖基化，半乳糖基化，鼠李糖基化和乳糖基化可以中等至极好的产率形成结构多样的O或S联寡糖和糖基化氨基酸。
• Glycosylation and Pyranose-Furanose Isomerization of Carbohydrates Using HClO₄-SiO₂: Synthesis of Oligosaccharides Containing Galactofuranose
  作者：Anup Misra、Chinmoy Mukherjee

  DOI：10.1055/s-2007-965913

  日期：2007.3

  A series of di- and trisaccharides containing 6-O-linked galactofuranose were synthesized as an anomeric mixture of methyl glycosides using silica-supported perchloric acid.

  一系列含有6-O-连接的呋喃半乳糖的二糖和三糖被合成，它们是以甲基糖苷的异头混合物形式，通过硅胶负载的高氯酸作为催化剂。
• Efficient glycosylation with glycosyl ortho-allylbenzoates as donors
  作者：Haijing Liang、Lixia Ma、Changwei Li、Qiang Peng、Zhaoyan Wang、Zhan-xin Zhang、Lan Yu、Huanxiang Liu、Fengli An、Weihua Xue

  DOI：10.1016/j.tetlet.2018.11.061

  日期：2019.1

  Glycosylation reactions are significant as they provide access to model compounds that are useful for elucidating biochemical pathways. Herein, we describe the development of glycosyl ortho-alkynylbenzoates as novel, bench-top stable, and readily available glycosyl donors. Glycosylation is promoted by inexpensive trimethylsilyl triflate (TMSOTf) in combination with N-iodosuccinimide (NIS) under mild

  糖基化反应很重要，因为它们提供了可用于阐明生化途径的模型化合物的途径。在本文中，我们描述了糖基邻炔基苯甲酸酯作为新型，台式稳定且易于获得的糖基供体的发展。廉价的三甲基甲硅烷基三氟甲磺酸酯（TMSOTf）与N-碘代琥珀酰亚胺（NIS）组合可在温和的反应条件下促进糖基化。因此，新型糖基供体是合成糖苷的有前途的试剂。