ethyl 4,6-di-O-benzyl-2-deoxy-3-tert-butylsilyl-2-trichloroacetamido-1-thio-β-D-glucopyranoside | 1429920-31-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4,6-di-O-benzyl-2-deoxy-3-tert-butylsilyl-2-trichloroacetamido-1-thio-β-D-glucopyranoside
• 英文别名: ethyl 4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-2-deoxy-2-trichloroacetamino-1-thio-β-D-glucopyranoside；N-[(2S,3R,4R,5R,6R)-4-[tert-butyl(dimethyl)silyl]oxy-2-ethylsulfanyl-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]-2,2,2-trichloroacetamide
• CAS: 1429920-31-9
• 化学式: C₃₀H₄₂Cl₃NO₅SSi
• 分子量: 663.178
• InChiKey: QIAODFYEYHWLHK-ACFIUOAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.51
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 4,6-di-O-benzyl-2-deoxy-3-tert-butylsilyl-2-trichloroacetamido-1-thio-β-D-glucopyranoside 在 吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 15.5h， 生成 ethyl 4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-3-fluorenylmethoxycarbonyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Total Synthesis of theEscherichia coliO111O-Specific Polysaccharide Repeating Unit

  摘要：

  AbstractThe first total synthesis of the O‐antigen pentasaccharide repeating unit from Gram‐negative bacteria Escherichia coli O111 was achieved starting from four monosaccharide building blocks. Key to the synthetic approach was a bis‐glycosylation reaction to combine trisaccharide 10 and colitose 5. The colitose building block (5) was obtained de novo from non‐carbohydrate precursors. The pentasaccharide was equipped at the reducing end with an amino spacer to provide a handle for subsequent conjugation to a carrier protein in anticipation of immunological studies.

  DOI：

  10.1002/chem.201204394
• 作为产物：
  描述：

  溴甲苯 、 叔丁基二甲基氯硅烷 、 ethyl 4,6-O-benzylidene-2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside 在 咪唑 、 硼烷四氢呋喃络合物 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以77%的产率得到ethyl 4,6-di-O-benzyl-2-deoxy-3-tert-butylsilyl-2-trichloroacetamido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Total Synthesis of theEscherichia coliO111O-Specific Polysaccharide Repeating Unit

  摘要：

  AbstractThe first total synthesis of the O‐antigen pentasaccharide repeating unit from Gram‐negative bacteria Escherichia coli O111 was achieved starting from four monosaccharide building blocks. Key to the synthetic approach was a bis‐glycosylation reaction to combine trisaccharide 10 and colitose 5. The colitose building block (5) was obtained de novo from non‐carbohydrate precursors. The pentasaccharide was equipped at the reducing end with an amino spacer to provide a handle for subsequent conjugation to a carrier protein in anticipation of immunological studies.

  DOI：

  10.1002/chem.201204394

文献信息

• Automated Glycan Assembly of Complex Oligosaccharides Related to Blood Group Determinants
  作者：Heung Sik Hahm、Chien-Fu Liang、Chian-Hui Lai、Richard J. Fair、Frank Schuhmacher、Peter H. Seeberger

  DOI：10.1021/acs.joc.6b00554

  日期：2016.7.15

  Lactotetraosyl (Lc4) and neo-lactotetraosyl (nLc4) are backbones that are common to many glycans. Using automated glycan assembly, these common core structures were constructed and elaborated to access synthetically challenging glycans of biological relevance. The incorporation of alpha-fucoses is demonstrated for H-type I and II; alpha(1,3)-galactose epitopes were prepared, and the pentasaccharide HNK-1 required incorporation of a 3-O-sulfate. In addition to preparing the target structures, essential insights were gained regarding the relationships of glycosylating agents and nucleophiles as well as the linker stability.