4-methylphenyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside | 1352561-57-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylphenyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside
• 英文别名: p-tolyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-levulinyl-1-thio-β-D-glucopyranoside；[(2S,3R,4S,5R,6R)-2-(4-methylphenyl)sulfanyl-5-(4-oxopentanoyloxy)-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
• CAS: 1352561-57-9
• 化学式: C₃₉H₄₀O₈S
• 分子量: 668.808
• InChiKey: LAWNCSPUCFKUTI-IMVXAUIJSA-N

物化性质

• 沸点：
  773.1±60.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-methylphenyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 一水合肼 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 6-azidohexyl 2-O-benzoyl-3,6-di-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Exploring and Exploiting the Reactivity of Glucuronic Acid Donors

  摘要：

  The relative reactivity of glucuronic acid esters was established in a series of competition experiments, in which two thioglucoside and/or thioglucuronic acid ester donors competed for a limited amount of activator (NIS-TfOH). Although glucuronic add esters are often considered to be of very low reactivity, the series of competition reactions revealed that the reactivity of the glucuronic acid esters studied is sufficient to provide productive glycosylation reactions. The latter is illustrated in the synthesis of two Streptococcus pneumoniae trisaccharides, in which the applicability of the two similarly protected frame-shifted thiociisaccharide donors, Glc-GlcA and GlcA-Glc, were compared. The Glc-GlcA disaccharide, featuring the glucuronic acid donor moiety, proved to be the most productive in the assembly of a protected S. pneumoniae trisaccharide.

  DOI：

  10.1021/jo201586r
• 作为产物：
  描述：

  3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 在 三乙基硅烷 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 sodium methylate 、 对甲苯磺酸 、 三氟乙酸 、 三氟乙酸酐 、 N,N'-二异丙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 301.0h， 生成 4-methylphenyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Automated glycan assembly of a S. pneumoniae serotype 3 CPS antigen

  摘要：

  针对导致严重疾病的最常见细菌感染之一的肺炎球菌的疫苗依赖于与蛋白质结合的分离的胶囊多糖（CPS）。这种分离物包含不同链长和框移的异质寡糖混合物。获得定义明确的合成肺炎球菌CPS结构是可取的。已知的肺炎球菌3型CPS的合成依赖于耗时且产率低的后期氧化步骤，或者使用二糖建筑块，这限制了变异性。在这里，我们报告了第一个迭代自动糖基组装（AGA）的可结合的肺炎球菌3型CPS三糖的组装。使用一种新型葡萄糖醛酸建筑块组装了这种寡糖，以避免需要后期氧化。在每个糖基化周期之前引入一个活化剂的洗涤步骤大大增加了产量，通过中和合成周期中去保护步骤中的任何残留碱。这个工艺改进适用于许多其他寡糖的AGA。

  DOI：

  10.3762/bjoc.12.139

文献信息

• Total Synthesis of Phellinus ribis Glycans with Immunostimulating Activities by an Orthogonal One-Pot Glycosylation Strategy
  作者：Jie Wan、Leilei Wang、Guozhi Xiao

  DOI：10.1055/a-1969-3992

  日期：2023.2

  achieved, which features orthogonal one-pot glycosylation strategy on the basis of N-phenyltrifluoroacetimidate (PTFAI) glycosylation, Yu glycosylation and ortho-(1-phenylvinyl)benzoate (PVB) glycosylation. The issues inherent to thioglycosides-based orthogonal one-pot glycosylation such as aglycone transfer have been precluded by this one-pot glycosylation strategy, which can streamline glycans chemical

  已经实现了具有强免疫刺激活性的桑黄聚糖的九糖重复单元和较短序列的全合成，其特点是基于 N-苯基三氟乙酰亚胺酯 (PTFAI) 糖基化、Yu 糖基化和邻位-(1-) 的正交一锅糖基化策略苯乙烯基）苯甲酸酯 (PVB) 糖基化。这种一锅糖基化策略排除了基于硫糖苷的正交一锅糖基化（如糖苷配基转移）所固有的问题，它可以简化聚糖的化学合成。
• Automated glycan assembly of a <i>S. pneumoniae</i> serotype 3 CPS antigen
  作者：Markus W Weishaupt、Stefan Matthies、Mattan Hurevich、Claney L Pereira、Heung Sik Hahm、Peter H Seeberger

  DOI：10.3762/bjoc.12.139

  日期：——

  Vaccines against S. pneumoniae, one of the most prevalent bacterial infections causing severe disease, rely on isolated capsular polysaccharide (CPS) that are conjugated to proteins. Such isolates contain a heterogeneous oligosaccharide mixture of different chain lengths and frame shifts. Access to defined synthetic S. pneumoniae CPS structures is desirable. Known syntheses of S. pneumoniae serotype 3 CPS rely on a time-consuming and low-yielding late-stage oxidation step, or use disaccharide building blocks which limits variability. Herein, we report the first iterative automated glycan assembly (AGA) of a conjugation-ready S. pneumoniae serotype 3 CPS trisaccharide. This oligosaccharide was assembled using a novel glucuronic acid building block to circumvent the need for a late-stage oxidation. The introduction of a washing step with the activator prior to each glycosylation cycle greatly increased the yields by neutralizing any residual base from deprotection steps in the synthetic cycle. This process improvement is applicable to AGA of many other oligosaccharides.

  针对导致严重疾病的最常见细菌感染之一的肺炎球菌的疫苗依赖于与蛋白质结合的分离的胶囊多糖（CPS）。这种分离物包含不同链长和框移的异质寡糖混合物。获得定义明确的合成肺炎球菌CPS结构是可取的。已知的肺炎球菌3型CPS的合成依赖于耗时且产率低的后期氧化步骤，或者使用二糖建筑块，这限制了变异性。在这里，我们报告了第一个迭代自动糖基组装（AGA）的可结合的肺炎球菌3型CPS三糖的组装。使用一种新型葡萄糖醛酸建筑块组装了这种寡糖，以避免需要后期氧化。在每个糖基化周期之前引入一个活化剂的洗涤步骤大大增加了产量，通过中和合成周期中去保护步骤中的任何残留碱。这个工艺改进适用于许多其他寡糖的AGA。
• Exploring and Exploiting the Reactivity of Glucuronic Acid Donors
  作者：Ana-Rae de Jong、Bas Hagen、Vincent van der Ark、Herman S. Overkleeft、Jeroen D. C. Codée、Gijsbert A. Van der Marel

  DOI：10.1021/jo201586r

  日期：2012.1.6

  The relative reactivity of glucuronic acid esters was established in a series of competition experiments, in which two thioglucoside and/or thioglucuronic acid ester donors competed for a limited amount of activator (NIS-TfOH). Although glucuronic add esters are often considered to be of very low reactivity, the series of competition reactions revealed that the reactivity of the glucuronic acid esters studied is sufficient to provide productive glycosylation reactions. The latter is illustrated in the synthesis of two Streptococcus pneumoniae trisaccharides, in which the applicability of the two similarly protected frame-shifted thiociisaccharide donors, Glc-GlcA and GlcA-Glc, were compared. The Glc-GlcA disaccharide, featuring the glucuronic acid donor moiety, proved to be the most productive in the assembly of a protected S. pneumoniae trisaccharide.