p-tolyl 2-O-benzoyl-3-O-tert-butyldimethylsilyl-4,6-O-dibenzyl-1-thio-β-D-galactopyranosidede | 1269466-90-1

• 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-3-O-tert-butyldimethylsilyl-4,6-O-dibenzyl-1-thio-β-D-galactopyranosidede
• 英文别名: p-methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside；[(2S,3R,4S,5S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-2-(4-methylphenyl)sulfanyl-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
• CAS: 1269466-90-1
• 化学式: C₄₀H₄₈O₆SSi
• 分子量: 684.969
• InChiKey: CGJRECJSQIBMNL-LZEMFQRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.23
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-tolyl 2-O-benzoyl-3-O-tert-butyldimethylsilyl-4,6-O-dibenzyl-1-thio-β-D-galactopyranosidede 在 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以84%的产率得到p-tolyl 2-O-benzoyl-4,6-O-dibenzyl-1-thio-β-D-galactopyranosidede
  参考文献：
  名称：

  Automated Glycan Assembly of Oligosaccharides Related to Arabinogalactan Proteins

  摘要：

  Arabinogalactan proteins are heavily glycosylated proteoglycans in plants. Their glycan portion consists of type-II arabinogalactan polysaccharides whose heterogeneity hampers the assignment of the arabinogalactan protein function. Synthetic chemistry is key to the procurement of molecular probes for plant biologists. Described is the automated glycan assembly of 14 oligosaccharides from four monosaccharide building blocks. These linear and branched glycans represent key structural features of natural type-II arabinogalactans and will serve as tools for arabinogalactan biology.

  DOI：

  10.1021/acs.orglett.5b02185
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 咪唑 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 、 三乙胺 、 diborane(6) 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 、 mineral oil 为溶剂， 反应 20.83h， 生成 p-tolyl 2-O-benzoyl-3-O-tert-butyldimethylsilyl-4,6-O-dibenzyl-1-thio-β-D-galactopyranosidede
  参考文献：
  名称：

  Automated Glycan Assembly of Oligosaccharides Related to Arabinogalactan Proteins

  摘要：

  Arabinogalactan proteins are heavily glycosylated proteoglycans in plants. Their glycan portion consists of type-II arabinogalactan polysaccharides whose heterogeneity hampers the assignment of the arabinogalactan protein function. Synthetic chemistry is key to the procurement of molecular probes for plant biologists. Described is the automated glycan assembly of 14 oligosaccharides from four monosaccharide building blocks. These linear and branched glycans represent key structural features of natural type-II arabinogalactans and will serve as tools for arabinogalactan biology.

  DOI：

  10.1021/acs.orglett.5b02185

文献信息

• One-Pot Strategies for the Synthesis of the Tetrasaccharide Linkage Region of Proteoglycans
  作者：Teng-Yi Huang、Medel Manuel L. Zulueta、Shang-Cheng Hung

  DOI：10.1021/ol200192d

  日期：2011.3.18

  tetrasaccharide corresponding to the linkage region of proteoglycans was synthesized via one-pot procedures from the silylated monosaccharide derivatives. Regioselective one-pot protection protocols were applied in generating the requisite monosaccharide building blocks whereas stereoselective one-pot glycosylation approaches were utilized to assemble the tetrasaccharide skeleton.

  通过一锅法从甲硅烷基化的单糖衍生物合成了与蛋白聚糖的连接区域相对应的连接有连接剂的四糖。区域选择性一锅保护方案被用于生成必要的单糖结构单元，而立体选择性一锅糖基化方法被用于组装四糖骨架。
• Acyl and Silyl Group Effects in Reactivity-Based One-Pot Glycosylation: Synthesis of Embryonic Stem Cell Surface Carbohydrates Lc₄ and IV²Fuc-Lc₄
  作者：Yun Hsu、Xin-An Lu、Medel Manuel L. Zulueta、Chih-Ming Tsai、Kuo-I Lin、Shang-Cheng Hung、Chi-Huey Wong

  DOI：10.1021/ja300284x

  日期：2012.3.14

  Relative reactivity evaluations showed the graded arming of toluenyl thioglucosides by variously positioned silyl groups but not by their acyl counterparts. These findings were applied in reactivity-based one-pot assembly of linker-attached Lc(4) and IV(2)Fuc-Lc(4), which are components of human embryonic stem cell surface. The sugar-galectin-1 binding was also examined.
• Automated Glycan Assembly of Oligosaccharides Related to Arabinogalactan Proteins
  作者：Max P. Bartetzko、Frank Schuhmacher、Heung Sik Hahm、Peter H. Seeberger、Fabian Pfrengle

  DOI：10.1021/acs.orglett.5b02185

  日期：2015.9.4

  Arabinogalactan proteins are heavily glycosylated proteoglycans in plants. Their glycan portion consists of type-II arabinogalactan polysaccharides whose heterogeneity hampers the assignment of the arabinogalactan protein function. Synthetic chemistry is key to the procurement of molecular probes for plant biologists. Described is the automated glycan assembly of 14 oligosaccharides from four monosaccharide building blocks. These linear and branched glycans represent key structural features of natural type-II arabinogalactans and will serve as tools for arabinogalactan biology.