(2-methyl-5-tert-butylphenyl) 1-thio-α-D-mannopyranoside | 1361016-58-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-methyl-5-tert-butylphenyl) 1-thio-α-D-mannopyranoside
• 英文别名: (2-methyl-5-tert-butylphenyl) 1-thia-α-D-mannopyranoside
• CAS: 1361016-58-1
• 化学式: C₁₇H₂₆O₅S
• 分子量: 342.456
• InChiKey: PWMRGTXMBSQPAT-NZBFACKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.18
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  90.15
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2-methyl-5-tert-butylphenyl) 1-thio-α-D-mannopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 mineral oil 为溶剂， 反应 10.83h， 生成 (2-methyl-5-tert-butylthiophenyl) 4,6-di-O-benzyl-2-O-benzoyl-3-O-chloroacetyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  与肺炎克雷伯菌 O3 血清型脂多糖 O 抗原结构相关的甲基磷酸化寡甘露糖苷的合成及其在兔和人血清中特异性抗体检测中的应用

  摘要：

  合成了与 O3 血清型肺炎克雷伯菌的脂多糖 (LPS) O 抗原结构相关的甲基磷酸化单甘露糖苷、二甘露糖苷和三甘露糖苷，并与生物素标签缀合。使用均匀的单糖合成嵌段进行目标碳水化合物链的立体和区域选择性组装。之后，通过与甲基-H-膦酸酯试剂偶联引入甲基磷酸基团，然后氧化和脱保护，得到目标寡糖。所得化合物的1 H 和13 C NMR谱与相应天然多糖的谱图吻合良好。新制备的生物素化寡糖以及先前报道的与肺炎克雷伯菌LPS的半乳聚糖I和半乳聚糖II相关的生物素化糖缀合物用于ELISA检测抗肺炎克雷伯菌兔血清中的抗体。抗O3血清抗体特异性识别具有末端甲基磷酸甘露糖基残基的合成寡糖配体，而抗O1血清抗体识别与肺炎克雷伯菌半乳聚糖II相关的寡糖。对确诊克雷伯氏菌感染患者的人体血清分析也表明，临床病例中存在针对合成寡糖的抗体。因此，所描述的化合物与其他克雷伯氏菌相关的抗原寡糖一起可以潜在地用作肺炎克雷伯氏菌

  DOI：

  10.1039/d3ob01203d
• 作为产物：
  描述：

  (2-methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-acetyl-1-thia-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以100%的产率得到(2-methyl-5-tert-butylphenyl) 1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Improved methods for the stereoselective synthesis of mannoheptosyl donors and their glycosides: toward the synthesis of the trisaccharide repeating unit of the Campylobacter jejuni RM1221 capsular polysaccharide

  摘要：

  In view of the importance of 6-deoxymannoheptosides as structural units in the Campylobacter jejuni RM1221 capsular polysaccharide, the development of effective synthetic protocols for 4-O-6-S-alpha-cyanobenzylidene thio-o-mannoheptapyranoside donors carrying either 3-O-naphthylmethyl or 3-O-acetyl groups is described starting from D-mannose. In particular, tris(phenylthio)methyllithium is found to undergo highly stereoselective addition to a mannose-6-aldehyde in sharp contrast to the vinyl Grignard reagent whose reactions were essentially devoid of selectivity. A brief survey of coupling reactions with the two donors indicted the 3-O-acetyl system to be highly alpha-selective whereas the 3-O-naphthylmethyl congener was highly beta-selective indicating that the presence of the seventh carbon atom in these donors is not detrimental to coupling selectivity in either instance. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.094

文献信息

• Highly convergent synthesis of a β-mannuronic acid alginate hexadecasaccharide
  作者：Dingyi Pan、Liangliang Zhang、Qingting Hua、You Yang

  DOI：10.1039/c9ob01254k

  日期：——

  Solution-phase synthesis of poly-β-mannuronic acids still remains unexplored. We report the first synthesis of a β-mannuronic acid alginate hexadecasaccharide representing the longest synthetic polymannuronic acid so far. The highly convergent synthetic approach provides a new avenue to access poly-β-mannuronic acids that can enable the biological evaluation of poly-β-mannuronic acids as potential

  聚-β-甘露糖醛酸的溶液相合成仍未探索。我们报道了迄今为止合成时间最长的β-甘露糖醛酸海藻酸酯十六烷基糖的首次合成。高度收敛的合成方法为获取聚β-甘露糖醛酸提供了一条新途径，可以使聚β-甘露糖醛酸作为潜在的治疗剂和疫苗进行生物学评估。
• Iron(III)-Triflate-Catalyzed Multiple Glycosylations with Peracetylated β-d-Glucosamine
  作者：Amandine Xolin、Stéphanie Norsikian、François-Didier Boyer、Jean-Marie Beau

  DOI：10.1002/ejoc.201600457

  日期：2016.7

  Direct multiple glycosylations of thioaryl and propargyl mannopyranosides with peracetylated β-d-glucosamine have been carried out using catalytic iron(III) triflate as a promoter in the presence of 2,4,6-tri-tert-butylpyrimidine under microwave irradiation. This has led to the one-step formation of various oligosaccharides with mannose at the branching point. Subsequent direct introduction of a linker

  在微波辐射下，在 2,4,6-三叔丁基嘧啶存在下，使用催化三氟甲磺酸铁 (III) 作为促进剂，硫代芳基和炔丙基吡喃甘露糖苷与过乙酰化 β-d-葡糖胺进行了直接多重糖基化。这导致在分支点处一步形成具有甘露糖的各种寡糖。随后通过铜催化的叠氮化物-炔烃环加成与炔丙基支链聚糖和最终脱保护直接引入接头，从而快速获得 N-聚糖模拟物。
• Mantyl tagged oligo α (1 → 2) mannosides as Candida albicans β-mannosyl transferases substrates: a comparison between synthetic strategies
  作者：Marilyne Pourcelot、Laurent Cattiaux、Ghenima Sfihi-Loualia、Emeline Fabre、Frédéric Krzewinski、Chantal Fradin、Daniel Poulain、Florence Delplace、Yann Guérardel、Jean-Maurice Mallet

  DOI：10.1039/c3ra43340d

  日期：——

  Fluorescent oligomannosides are important tools for the evaluation of mannosyl transferase activities and selectivities. In a project dealing with Candida albicans β-mannosyl transferases, three mantyl tagged α (1 → 2) oligomannosides were prepared by different ways: using all ester strategy compatible with the presence of an azido group suitable for direct click chemistry; and alternatively using the more classic benzyl protecting groups. Although more elegant, the all ester strategy has shown important limitations: reduced reactivity of mannosyl donors, and 3 → 2 ester migration. Preliminary enzymatic studies have shown that the synthetic oligomannosides are efficient substrate of β-mannosyl transferases.

  荧光寡甘露糖苷是评估甘露基转移酶活性和选择性的重要工具。在一个研究白色念珠菌δ-甘露糖基转移酶的项目中，通过不同的方法制备了三种曼特基标记的δ（1â2）低聚甘露糖苷：使用与叠氮基团兼容的全酯策略，适合直接点击化学；或者使用更经典的苄基保护基团。尽管全酯策略更为优雅，但也显示出重要的局限性：甘露糖苷供体的反应性降低，以及 3 - 2 酯迁移。初步的酶学研究表明，合成的低聚甘露糖苷是δ-甘露糖苷转移酶的有效底物。
• Biotin sulfone tagged oligomannosides as immunogens for eliciting antibodies against specific mannan epitopes
  作者：Guillaume Despras、Raymond Robert、Boualem Sendid、Emeline Machez、Daniel Poulain、Jean-Maurice Mallet

  DOI：10.1016/j.bmc.2011.12.048

  日期：2012.3

  Biotinylated tri and tetrasaccharide: alpha Man (1 -> 3) alpha Man (1 -> 2) alpha Man; alpha Man (1 -> 3) alpha Man (1 -> 2) alpha Man (1 -> 2) alpha Man were prepared using methyl tertbutyl phenyl thioglycosides glycosyl donors (MBP) and biotin sulfone strategy. Three key mannosyl thioglycosidic donors have been prepared: one for 1 -> 2 linkage and two for the 1 -> 3 linkage (protected with a 4,6-O-benzylidene or a 4,6-di-O-benzyl). The benzyliden protected one was not found reactive enough, and the benzylated donor was preferred. These biotinylated oligomanosides were evaluated as antigen in Crohn disease diagnosis and used coupled to streptavidin as hapten for eliciting polyclonal antibodies in mice. (C) 2011 Elsevier Ltd. All rights reserved.