ethyl 4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-3-fluorenylmethoxycarbonyl-1-thio-β-D-glucopyranoside | 1429920-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: ethyl 4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-3-fluorenylmethoxycarbonyl-1-thio-β-D-glucopyranoside
• 英文别名: ethyl 4,6-di-O-benzyl-3-O-fluorenylmethoxycarbonyl-2-deoxy-2-trichloroacetamino-1-thio-β-D-glucopyranoside；[(2S,3R,4R,5S,6R)-2-ethylsulfanyl-5-phenylmethoxy-6-(phenylmethoxymethyl)-3-[(2,2,2-trichloroacetyl)amino]oxan-4-yl] 9H-fluoren-9-ylmethyl carbonate
• CAS: 1429920-32-0
• 化学式: C₃₉H₃₈Cl₃NO₇S
• 分子量: 771.158
• InChiKey: POQOWWWNBWVWEV-HFDGEQGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  51
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-3-fluorenylmethoxycarbonyl-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 生成 N-(benzyl)benzyloxycarbonyl-5-aminopentanyl-4,6-di-O-benzyl-2-trichloroacetamido-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：

  ethyl 4,6-O-benzylidene-2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside 在 吡啶 、 咪唑 、 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

文献信息

• Combination of automated solid-phase and enzymatic oligosaccharide synthesis provides access to α(2,3)-sialylated glycans
  作者：Richard J. Fair、Heung Sik Hahm、Peter H. Seeberger

  DOI：10.1039/c5cc01368b

  日期：——

  A synthetic strategy combining automated solid-phase chemical synthesis and enzymatic sialylation was developed to access α(2,3)-sialylated glycans.

  一种合成策略结合了自动化固相化学合成和酶促唾液酸化，用于制备α（2,3）-唾液酸化的糖基。
• 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.
• Total Synthesis of the<i>Escherichia coli</i>O111<i>O</i>-Specific Polysaccharide Repeating Unit
  作者：Oliviana Calin、Steffen Eller、Heung Sik Hahm、Peter H. Seeberger

  DOI：10.1002/chem.201204394

  日期：2013.3.18

  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.