p-tolyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-glucopyranoside | 1352561-53-5

• 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-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3-acetyloxy-6-(4-methylphenyl)sulfanyl-4,5-bis(phenylmethoxy)oxan-2-yl]methyl acetate
• CAS: 1352561-53-5
• 化学式: C₃₁H₃₄O₇S
• 分子量: 550.673
• InChiKey: QWQGIVFJZWRWOY-SAEUYMBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  p-tolyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-glucopyranoside 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.03h， 生成 p-methoxyphenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl-(1→2)-6-O-benzyl-3-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Concise synthesis of the trisaccharide repeating unit of the O-polysaccharide from Aeromonas hydrophila A19 (O:14)

  摘要：

  Chemical synthesis of the trisaccharide repeating unit of the O-polysaccharide from Aeromonas hydrophila A19 (O:14) is reported in the form of its p-methoxyphenyl glycosides. Suitably protected monosaccharide synthons were prepared either by literature procedure or by strategies developed in house. Stereoselective glycosylations were accomplished by the activation of thioglycosides using N-iodosuccinimide in conjunction with H2SO4-silica in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.06.009
• 作为产物：
  描述：

  乙酸酐 、 p-tolyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside 在 吡啶 作用下， 反应 2.0h， 以93%的产率得到p-tolyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Concise synthesis of the trisaccharide repeating unit of the O-polysaccharide from Aeromonas hydrophila A19 (O:14)

  摘要：

  Chemical synthesis of the trisaccharide repeating unit of the O-polysaccharide from Aeromonas hydrophila A19 (O:14) is reported in the form of its p-methoxyphenyl glycosides. Suitably protected monosaccharide synthons were prepared either by literature procedure or by strategies developed in house. Stereoselective glycosylations were accomplished by the activation of thioglycosides using N-iodosuccinimide in conjunction with H2SO4-silica in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.06.009

文献信息

• 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.