p-tolyl 4,6-O-benzylidene-3-O-(naphthalene-2-ylmethyl)-1-thio-β-D-glucopyranoside | 942043-54-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 4,6-O-benzylidene-3-O-(naphthalene-2-ylmethyl)-1-thio-β-D-glucopyranoside
• 英文别名: p-methylphenyl 4,6-O-benzylidine-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside；p-tolyl 4,6-O-benzylidene-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside；(2R,4aR,6S,7R,8R,8aR)-6-(4-methylphenyl)sulfanyl-8-(naphthalen-2-ylmethoxy)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 942043-54-1
• 化学式: C₃₁H₃₀O₅S
• 分子量: 514.642
• InChiKey: WQDDYNMRGYUILP-NHMJYFFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-tolyl 4,6-O-benzylidene-3-O-(naphthalene-2-ylmethyl)-1-thio-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 、 水 为溶剂， 生成
  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：

  4-methylphenyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 18.0h， 生成 p-tolyl 4,6-O-benzylidene-3-O-(naphthalene-2-ylmethyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  β-葡聚糖线性低聚糖作为抗真菌疫苗开发的抗原的合成和免疫学研究

  摘要：

  抗真菌疫苗最近引起了人们的强烈兴趣，以抵消真菌感染的复发。在这种情况下，在所有真菌细胞表面上充分表达，对真菌具有功能性和免疫活性的β-葡聚糖是有吸引力的靶抗原。为了开发基于β-葡聚糖的有效抗真菌疫苗，设计，合成了一系列寡糖衍生物，并将其与载体蛋白匙孔戚血蓝蛋白（KLH）结合，形成了新的半合成糖缀合物疫苗。在本文中，针对设计的寡糖，开发了一种基于预激活的迭代糖基化方法的收敛有效的合成策略。该策略可用于快速构建以较短的寡糖为构建基的大型低聚β-葡聚糖。合成的β-葡聚糖六糖，八糖，十糖和十二糖的KLH共轭物可在小鼠中引发高滴度的抗原特异性总抗体和IgG抗体，提示诱导功能性T细胞介导的免疫。此外，还发现八-，十-和十二-β-葡聚糖比六聚体具有更高的免疫原性，并且八聚体是其中最好的。结果表明，优异的免疫原性所需的最佳β-葡聚糖寡糖序列是七聚体或八聚体，较长的葡聚糖不一定是更好的抗原，这一发现可能具有

  DOI：

  10.1021/bc500575a

文献信息

• Synergistic Glycosylation as Key to the Chemical Synthesis of an Outer Core Octasaccharide of<i>Helicobacter pylori</i>
  作者：Xiaopeng Zou、Chunjun Qin、Claney L. Pereira、Guangzong Tian、Jing Hu、Peter H. Seeberger、Jian Yin

  DOI：10.1002/chem.201800049

  日期：2018.2.26

  a [3+5] convergent synthesis of an outer core octasaccharide of H. pylori employing just three orthogonally protected building blocks. A synergistic glycosylation strategy enables the creation of five pivotal 1,2‐cis‐α‐glucosidic bonds consist of four types of linkages using just three monomers. This strategy can be expanded to many 1,2‐cis‐α‐gluoside‐containing oligosaccharides both in solution and

  幽门螺杆菌是一种广泛的胃细菌病原体，在发展中国家感染90％的人口，可引起慢性胃炎，消化性溃疡和胃癌。作战幽门螺旋杆菌感染是一个严重的挑战，因为对抗生素的抗性增加和缺乏疫苗。覆盖幽门螺杆菌细胞表面外膜的脂多糖是糖缀合物疫苗开发的诱人靶标。在这里，我们报告幽门螺杆菌的外部核心八糖的[3 + 5]会聚合成，仅使用三个正交保护的构建基块。协同糖基化策略可创建五个关键的1,2-顺式-α-糖苷键仅使用三种单体就由四种类型的键组成。该策略可以扩展到溶液和固相中的许多含1,2-顺式-α-葡糖苷的寡糖。
• METHOD FOR PREPARING HEXOSE DERIVATIVES
  申请人：Hung Shang Cheng

  公开号：US20090105466A1

  公开（公告）日：2009-04-23

  A method for preparing hexose derivatives comprises the steps of providing a silylated hexose, treating the silylated hexose with a first carbonyl compound in the presence of a catalyst to form an ketalized hexose, treating the ketalized hexose with a second carbonyl compound followed by treating with a first reductant to form an etherized hexose, and converting the etherized hexose into a target hexose derivative, which can be 2-alcohol hexose, 3-alcohol hexose, 4-alcohol hexose, or a 6-alcohol hexose. In particular, the present invention can prepare the hexose derivatives with highly regioselective scheme to protect individual hydroxyls of monosaccharide units and install an orthogonal protecting group pattern in a one-pot manner

  制备己糖衍生物的方法包括以下步骤：提供硅烷基化的己糖，将硅烷基化的己糖与第一羰基化合物在催化剂存在下处理，形成缩酮化的己糖，将缩酮化的己糖与第二羰基化合物处理后，再用第一还原剂处理，形成醚化的己糖，并将醚化的己糖转化为目标己糖衍生物，可以是2-醇己糖、3-醇己糖、4-醇己糖或6-醇己糖。具体来说，本发明可以采用高度选择性的方案制备己糖衍生物，以保护单糖单元的各个羟基，并以一锅法安装正交保护基图案。
• Unusually Stable Picoloyl-Protected Trimethylsilyl Glycosides for Nonsymmetrical 1,1′-Glycosylation and Synthesis of 1,1′-Disaccharides with Diverse Configurations
  作者：Yen-Chu Luke Lu、Bhaswati Ghosh、Kwok-Kong Tony Mong

  DOI：10.1002/chem.201700785

  日期：2017.5.17

  Nonsymmetrical 1,1′-disaccharides and related derivatives constitute structural components in various glycolipids and natural products. Some of these compounds have been shown to exhibit appealing biological properties. We report a direct yet stereoselective 1,1′-glycosylation strategy for the synthesis of nonsymmetrical 1,1′-disaccharides with diverse configurations and sugar components. The strategy

  非对称的1,1'-二糖和相关衍生物构成各种糖脂和天然产物中的结构成分。这些化合物中的某些已显示出具有吸引力的生物学特性。我们报告了具有不同构型和糖成分的非对称1,1'-二糖合成的直接但立体选择性1,1'-糖基化策略。该策略基于新型构型稳定的糖苷受体和立体定向硫糖苷供体的联合作用。新的糖苷受体在远端C4 / C3位置具有一个皮甲酰基（Pico）保护基，可在酸性条件下赋予TMS糖苷异常的稳定性。
• Synthesis of a core trisaccharide building block for the assembly of N-glycan neoconjugates
  作者：Sonia Serna、Bharat Kardak、Niels-Christian Reichardt、Manuel Martin-Lomas

  DOI：10.1016/j.tetasy.2009.02.028

  日期：2009.5

  A short and high yielding synthesis of a core trisaccharide 1 as the key building block in the assembly of a library of N-glycan neoconjugates is presented. The beta-D-Manp-(1 -> 4)-D-GlcpNAc linkage was introduced by inversion of the C-2 position of a beta-glucoside. The glucosyl donor was efficiently synthesised following a recently published one-pot strategy. 2-Naphthylmethyl and benzylidene-acetal protection in the terminal mannose permitted selective liberation of main branching sites for subsequent glycosylation. A C5 azido linker attached to the anomeric position, which is stable throughout the synthesis, will allow for the posterior immobilisation of deprotected glycans on a microarray surface. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.