1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-(tosyloxymethyl)-β-D-glucopyranose | 1338463-77-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-(tosyloxymethyl)-β-D-glucopyranose
• CAS: 1338463-77-6
• 化学式: C₂₉H₃₄O₁₃S
• 分子量: 622.647
• InChiKey: RWFNIWOXMFOMRG-RQKPWJHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  43.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  167.03
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-(tosyloxymethyl)-β-D-glucopyranose 在 N,O-双三甲硅基乙酰胺 、 20 % Pd(OH)2/C 、 氢气 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Design, Synthesis, and Properties of Boat-Shaped Glucopyranosyl Nucleic Acid

  摘要：

  A boat-shaped glucopyranosyl nucleic acid (BsNA) was synthesized to investigate the possibility that the lean of a nucleobase Is a factor affecting duplex-forming ability of oligonucleotides. From the crystal structure of a BsNA nucleoside and the thermal stability of duplex oligonucleotides, it was found that not only the lean of the base but also the rotation angle of the glycosidic bond axis were important factors in a stable duplex formation.

  DOI：

  10.1021/ol2025229
• 作为产物：
  描述：

  在 吡啶 、 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-(tosyloxymethyl)-β-D-glucopyranose
  参考文献：
  名称：

  Design, Synthesis, and Properties of Boat-Shaped Glucopyranosyl Nucleic Acid

  摘要：

  A boat-shaped glucopyranosyl nucleic acid (BsNA) was synthesized to investigate the possibility that the lean of a nucleobase Is a factor affecting duplex-forming ability of oligonucleotides. From the crystal structure of a BsNA nucleoside and the thermal stability of duplex oligonucleotides, it was found that not only the lean of the base but also the rotation angle of the glycosidic bond axis were important factors in a stable duplex formation.

  DOI：

  10.1021/ol2025229