4-methoxyphenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside | 13299-05-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside
• 英文别名: p-Methoxyphenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside；[(3R,4S,5R,6S)-4,5-diacetyloxy-6-(4-methoxyphenoxy)oxan-3-yl] acetate
• CAS: 13299-05-3
• 化学式: C₁₈H₂₂O₉
• 分子量: 382.367
• InChiKey: MKQVYQLMEWNXBF-XDNAFOTISA-N

物化性质

• 熔点：
  150.4 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  462.8±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 4-methoxyphenyl β-D-xylopyranoside
  参考文献：
  名称：

  木糖的芳基取代衍生物作为环保型多功能农药的应用

  摘要：

  已经合成了一系列木糖的芳基取代的衍生物。生物学测试表明，所得化合物对各种植物致病真菌具有很高的杀真菌活性。其他生物学研究表明，合成的化合物具有很高的植物生长调节活性。

  DOI：

  10.1134/s1070363216130120
• 作为产物：
  描述：

  D-吡喃木糖 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 氢溴酸 、 silver carbonate 作用下， 以 吡啶 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 生成 4-methoxyphenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  木糖的芳基取代衍生物作为环保型多功能农药的应用

  摘要：

  已经合成了一系列木糖的芳基取代的衍生物。生物学测试表明，所得化合物对各种植物致病真菌具有很高的杀真菌活性。其他生物学研究表明，合成的化合物具有很高的植物生长调节活性。

  DOI：

  10.1134/s1070363216130120

文献信息

• Synthesis of uronic acid-containing xylans found in wood and pulp
  作者：Stefan Oscarson、Pär Svahnberg

  DOI：10.1039/b009670a

  日期：——

  with two glucuronate thioglycoside donors differently substituted in the 4-position, O-methyl and O-mesyl, respectively, to give trisaccharides. DMTST as promoter in diethyl ether gives exclusively the α-linked products in high yield. Treatment of the 4″-O-mesyl trisaccharide with DBU then gives the α,β-unsaturated uronic acid derivative. The protection pattern introduced in the acceptor allows continued

  含两个糖醛酸 三糖，（4-脱氧β-大号-苏式-己-4- enopyranosyluronic酸） -和（4- ö甲基α- d -gluropyranosyluronic酸） - （1→2）-β- d -xylopyranosyl-（1 →4）-从纸浆中合成酶水解产物中发现的D-木吡喃糖。常见的二木糖苷2'-OH受体对甲氧基苯基[3,4- O-（2'，3'-二甲氧基丁烷-2'，3'-二基）-β- D-木吡喃糖基]-（1→4）-构建2，3-二-O-苯甲酰基-β - D-吡喃吡喃糖苷，并与在4-位不同取代的两个葡萄糖醛酸硫代糖苷供体，O-甲基和O-mesyl分别给出 三糖。DMTST作为中的启动子乙醚仅以高收率得到α-连接产物。然后用DBU处理4″ -O-甲磺酰基三糖，得到不饱和的α，β糖醛酸衍生物。受体中引入的保护模式可以继续合成更大的寡糖。除去丁二酮缩醛产生3'，4'-受体，并且对甲氧基苯基
• Total Synthesis of <i>Pseudomonas aeruginosa</i> 1244 Pilin Glycan via <i>de Novo</i> Synthesis of Pseudaminic Acid
  作者：Han Liu、Yanfeng Zhang、Ruohan Wei、Gloria Andolina、Xuechen Li

  DOI：10.1021/jacs.7b06055

  日期：2017.9.27

  synthesis involve the diastereoselective glycine thioester isonitrile-based aldol-type reaction to create the 1,3-anti-diamino skeleton, followed by the Fukuyama reduction and the indium-mediated Barbier-type allylation. Moreover, we have studied the glycosylation of the Pse glycosyl donors and identified the structural determinants for its glycosylation diastereoselectivity, which enabled us to complete

  假胺酸 (Pse) 是细菌物种特有的一种非洛糖酸，是各种病原体物种中重要的细胞表面聚糖和糖蛋白的组成部分，例如对医院造成严重威胁的铜绿假单胞菌 (Pseudomonas aeruginosa)。在此，我们介绍了从容易获得的 Cbz-l-异素苏氨酸甲酯（16 个步骤，产率 11%）开发 Pse 及其功能化衍生物的简便且可扩展的从头合成。我们从头合成中的关键反应涉及基于非对映选择性甘氨酸硫酯异腈的羟醛型反应，以创建 1,3-抗二氨基骨架，然后是 Fukuyama 还原和铟介导的 Barbier 型烯丙基化。此外，我们研究了 Pse 糖基供体的糖基化，并确定了其糖基化非对映选择性的结构决定因素，
• Lanthanum Trifluoromethane-sulfonate‐Catalyzed Facile Synthesis of Per‐<i>O</i>‐acetylated Sugars and Their One‐Pot Conversion to <i>S</i>‐Aryl and <i>O</i>‐Alkyl/Aryl Glycosides
  作者：Somnath Dasgupta‡、Vishal Kumar Rajput‡、Bimalendu Roy、Balaram Mukhopadhyay

  DOI：10.1080/07328300701298170

  日期：2007.4.30

  Lanthanum trifluoromethanesulfonate- catalyzed solvent-freeper-O-acetylation with stoichiometric acetic anhydride proceeds in high yield (95%-99%) to afford exclusively pyranose products as anomeric mixtures. Subsequent anomeric substitution employing borontrifluoride etherate and thiols or alcohols furnished the corresponding 1,2-trans-linked thioglycosides and O-glycosides, respectively, in good to excellent overall yield (75%-85%). Alternatively, reaction of free sugars in neat alcohol employing the same catalyst at elevated temperature gives the corresponding 1,2-cis-linked O-glycosides (along with 1,2-trans-linked glycosides as minor product) in good yield (73%-80%). Anomeric mixtures of compounds thus produced were characterized as their per-O-acetylated derivatives.[GRAPHICS]
• Enzymic .beta.-Galactosidation of Modified Monosaccharides: Study of the Enzyme Selectivity for the Acceptor and Its Application to the Synthesis of Disaccharides
  作者：Rosa Lopez、Alfonso Fernandez-Mayoralas

  DOI：10.1021/jo00083a013

  日期：1994.2

  The selectivity of the E. coli beta-galactosidase-catalyzed glycosylation of monosaccharides differently substituted at the anomeric position has been studied. Substituents bearing a phenyl ring increase the enzyme-acceptor binding; however, partial enzyme inhibition occurs. The regioselectivity of the glycosylation was dependent on small variations in the monosaccharide accceptor, such as the atom linked to the anomeric carbon and the number of methylenes between this atom and aromatic ring. A schematic model is proposed that accounts for the results. The information from this study allows the direct synthesis of disaccharides, with high regioselectivity and yields ranging from 30 to 40%.
• Synthetic Approach Toward the Partial Sequences of Betaglycan in the Linkage Region on Solid Support and in Solution Phase
  作者：Jun‐ichi Tamura、Akihiro Yamaguchi、Junko Tanaka、Yuko Nishimura

  DOI：10.1080/07328300701296810

  日期：2007.4.30

  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.