1-{2,4,6-tri-O-acetyl-3-O-benzyl-5-C-(tosyloxymethyl)-β-D-glucopyranosyl}thymine | 1338463-78-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-{2,4,6-tri-O-acetyl-3-O-benzyl-5-C-(tosyloxymethyl)-β-D-glucopyranosyl}thymine
• 英文别名: [(2S,3S,4S,5R,6R)-3,5-diacetyloxy-6-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-[(4-methylphenyl)sulfonyloxymethyl]-4-phenylmethoxyoxan-2-yl]methyl acetate
• CAS: 1338463-78-7
• 化学式: C₃₂H₃₆N₂O₁₃S
• 分子量: 688.709
• InChiKey: BPOQLWMDUACIEE-MILVSQPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  199
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1-{2,4,6-tri-O-acetyl-3-O-benzyl-5-C-(tosyloxymethyl)-β-D-glucopyranosyl}thymine 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三(三甲基硅基)硅烷 、 20 % Pd(OH)2/C 、 D(+)-10-樟脑磺酸 、 氢气 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 mineral oil 为溶剂， 反应 68.75h， 生成 1-(3-deoxy-2-O,5-C-methylene-β-D-glucopyranosyl)thymine
  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：

  1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-vinyl-β-D-glucopyranoside 在 吡啶 、 sodium tetrahydroborate 、 N,O-双三甲硅基乙酰胺 、 臭氧 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 22.0h， 生成 1-{2,4,6-tri-O-acetyl-3-O-benzyl-5-C-(tosyloxymethyl)-β-D-glucopyranosyl}thymine
  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

文献信息

• Synthesis and hybridization property of a boat-shaped pyranosyl nucleic acid containing an exocyclic methylene group in the sugar moiety
  作者：Kazuto Mori、Tetsuya Kodama、Satoshi Obika

  DOI：10.1016/j.bmc.2014.11.030

  日期：2015.1

  A boat-shaped pyranosyl nucleic acid (BsNA) having an exocyclic methylene group in the sugar moiety was synthesized to investigate the possibility that the axial H3′ of original BsNA is the cause of its duplex destabilization. The synthesized BsNA analog was chemically stable against various nucleophiles. From the thermal stability of duplex oligonucleotides including the BsNA analog, it was found

  合成了在糖部分具有环亚甲基的船形吡喃糖基核酸（BsNA），以研究原始BsNA的轴向H3'是其双链不稳定的原因。合成的BsNA类似物对各种亲核试剂具有化学稳定性。从包括BsNA类似物的双链体寡核苷酸的热稳定性，发现双链体形成能力对3'-位的官能团的大小敏感。
• Design, Synthesis, and Properties of Boat-Shaped Glucopyranosyl Nucleic Acid
  作者：Kazuto Mori、Tetsuya Kodama、Satoshi Obika

  DOI：10.1021/ol2025229

  日期：2011.11.18

  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.