p-tolyl 2-O-benzoyl-4-O-benzyl-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside | 942044-54-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 2-O-benzoyl-4-O-benzyl-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside
• CAS: 942044-54-4
• 化学式: C₃₈H₃₆O₆S
• 分子量: 620.766
• InChiKey: KLEVHIDFZPJOEE-DJCHGSEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.35
• 重原子数：
  45.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  p-tolyl 2-O-benzoyl-4-O-benzyl-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 benzyl (2S,3S,4S,5R,6S)-5-benzoyloxy-6-(4-methylphenyl)sulfanyl-4-(naphthalen-2-ylmethoxy)-3-phenylmethoxyoxane-2-carboxylate
  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：

  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 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 生成 p-tolyl 2-O-benzoyl-4-O-benzyl-3-O-(naphthalen-2-ylmethyl)-1-thio-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

文献信息

• A Convergent Synthesis of 6-<i>O</i>-Branched β-Glucan Oligosaccharides
  作者：Guochao Liao、Srinivas Burgula、Zhifang Zhou、Zhongwu Guo

  DOI：10.1002/ejoc.201500229

  日期：2015.5

  are important carbohydrate antigens on the surface of fungal cells useful for antifungal vaccine development. This paper has described a highly convergent and efficient strategy for the synthesis of structurally defined branched beta-glucan oligosaccharides that can be used for detailed studies of beta-glucans and for the design of beta-glucan-based vaccines. The strategy was highlighted by assembling

  β-葡聚糖是真菌细胞表面上重要的碳水化合物抗原，可用于开发抗真菌疫苗。本文描述了一种高度收敛和有效的策略，用于合成结构明确的支链β-葡聚糖低聚糖，可用于β-葡聚糖的详细研究和基于β-葡聚糖的疫苗的设计。通过以硫糖苷为糖基供体的基于预活化的糖基化组装标题化合物，突显了该策略。它被用来成功制备具有β-1,3-连接的非葡聚糖骨架的β-葡聚糖低聚糖，该主链在6位具有β-1,6-葡萄糖四糖，β-1,3-葡萄糖二糖和β-1,3-葡萄糖四糖分支。九葡聚糖中央糖单元的-O-位置。