p-tolyl 3,4-di-O-acetyl-2,6-dideoxy-1-thio-α-L-lyxo-hexopyranoside | 904285-74-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: p-tolyl 3,4-di-O-acetyl-2,6-dideoxy-1-thio-α-L-lyxo-hexopyranoside
• 英文别名: p-tolyl 3,4-di-O-acetyl-2-deoxy-1-thio-β-D-fucopyranoside
• CAS: 904285-74-1
• 化学式: C₁₇H₂₂O₅S
• 分子量: 338.425
• InChiKey: MOLIKMWRFOSFEZ-GNCDUGFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  p-tolyl 3,4-di-O-acetyl-2,6-dideoxy-1-thio-α-L-lyxo-hexopyranoside 在 palladium dihydroxide 、 三氟甲磺酸酐 1-(苯基亚硫酰基)哌啶 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 2,4,6-三叔丁基嘧啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 35.87h， 生成 n-octyl 2,6-dideoxy-α-L-lyxo-hexopyranosyl-(1->2)-3-amino-3-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of n-octyl 2,6-dideoxy-α-l-lyxo-hexopyranosyl-(1→2)-3-amino-3-deoxy-β-d-galactopyranoside, an analog of the H-disaccharide antigen

  摘要：

  The synthesis of an analog of the H-disaccharide antigen (2), in which the galactopyranosyl moiety bears an amino group at C-3 and the fucopyranosyl residue is deoxygenated at C-2, is reported. The key reaction in the preparation of 2 was the glycosylation of an appropriately protected n-octyl 3-azido-3-deoxy-galactopyranoside derivative with a 2,6-dideoxy thioglycoside promoted by 1-(phenylsulfinyl)piperidine and triflic anhydride. Disaccharide 2 is of interest in studies directed towards understanding the molecular basis of substrate recognition by the blood group A and B glycosyltransferases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.018
• 作为产物：
  描述：

  4-甲苯硫酚 、 2,6-脱水-1,5-二脱氧-L-阿拉伯-己-5-烯糖二乙酸酯 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以81%的产率得到p-tolyl 3,4-di-O-acetyl-2,6-dideoxy-1-thio-α-L-lyxo-hexopyranoside
  参考文献：
  名称：

  Synthesis of n-octyl 2,6-dideoxy-α-l-lyxo-hexopyranosyl-(1→2)-3-amino-3-deoxy-β-d-galactopyranoside, an analog of the H-disaccharide antigen

  摘要：

  The synthesis of an analog of the H-disaccharide antigen (2), in which the galactopyranosyl moiety bears an amino group at C-3 and the fucopyranosyl residue is deoxygenated at C-2, is reported. The key reaction in the preparation of 2 was the glycosylation of an appropriately protected n-octyl 3-azido-3-deoxy-galactopyranoside derivative with a 2,6-dideoxy thioglycoside promoted by 1-(phenylsulfinyl)piperidine and triflic anhydride. Disaccharide 2 is of interest in studies directed towards understanding the molecular basis of substrate recognition by the blood group A and B glycosyltransferases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.018

文献信息

• TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
  作者：Mei-Yuan Hsu、Yi-Pei Liu、Sarah Lam、Su-Ching Lin、Cheng-Chung Wang

  DOI：10.3762/bjoc.12.164

  日期：——

  The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective.

  甘露糖醛酸盐的硫加成反应可以在无溶剂条件下高效地通过等物量的溴化三甲基硅(TMSBr)催化产生良好至优异收率的S-2-脱氧糖苷。此外，加入三苯基膦氧化物作为添加剂，TMSBr介导的甘露糖醛酸盐与多种醇类的直接糖基化反应具有高度α-选择性。
• Glycosylation Enabled by Successive Rhodium(II) and Brønsted Acid Catalysis
  作者：Lingkui Meng、Peng Wu、Jing Fang、Ying Xiao、Xiong Xiao、Guangsheng Tu、Xiang Ma、Shuang Teng、Jing Zeng、Qian Wan

  DOI：10.1021/jacs.9b04619

  日期：2019.7.31

  reaction comprises two chronological meticulously-designed catalytic cycles: 1) rhodium-catalyzed formation of sulfonium ylide; 2) Brønsted acid-catalyzed formation of sulfonium ion. This protocol highlight-ed an effective and robust tactic to prepare glycosyl sulfonium ion from glycosyl sulfonium ylide precursor amenable for glycosylation.

  在此，我们报道了一种高效的糖基化反应，包括两个按时间顺序精心设计的催化循环：1）铑催化形成锍叶立德；2) Brønsted 酸催化形成锍离子。该协议强调了一种有效且稳健的策略，可从适合糖基化的糖基锍叶立德前体制备糖基锍离子。
• Short and efficient synthesis of a daunosamine donor from l-fucal
  作者：Markus Ohlin、Sophie Manner、Johanna Löfgren、Andrea Persson、Ulf Ellervik

  DOI：10.1039/c4ra01056f

  日期：——

  usually the aminosugar daunosamine. The anthracyclines are efficient chemotherapeutic agents against cancer, but their use is limited due to cardiotoxicity and induction of multidrug resistance. In the search for new anthracycline analogs, a daunosamine donor that can be used to glycosylate suitable aglycons is of utmost importance. Here, we present a short and efficient synthesis of the versatile donor

  蒽环霉素，例如柔红霉素，阿霉素和柔红霉素，由四环素部分组成，该四环素部分通过糖苷键与糖残基（通常是氨基糖柔红胺）相连。蒽环类药物是有效的抗癌化疗药物，但由于心脏毒性和诱发多药耐药性，其使用受到限制。在寻找新的蒽环类类似物时，最重要的是可用于糖基化合适的糖苷配基的柔红胺供体。在这里，我们从商业上的3个步骤中提出了一种短而有效的通用供体对甲苯基4-甲苯基4 - O-乙酰基-3-叠氮基2,3,6-三苯氧基-1-硫代-α- L -lyxo-己吡喃糖苷的合成可用L-fucal，总产率为32％。可以使用相同的方法从L-合成总收率28％的供体对甲苯基4 - O-乙酰基-3-叠氮基2,3,6-三苯氧基-1-硫代-α - L-阿拉伯糖基吡喃糖苷。鼠李糖，用于合成表柔比星类似物。