N⁶-Hexyl-2',3',5'-tri-O-benzoyladenosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N⁶-Hexyl-2',3',5'-tri-O-benzoyladenosine
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-[6-(hexylamino)purin-9-yl]oxolan-2-yl]methyl benzoate
• 化学式: C₃₇H₃₇N₅O₇
• 分子量: 663.73
• InChiKey: IFTHGIURPFJXDY-UTBAFCPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  49
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  卡培他滨杂质25 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 吡啶 、 4 A molecular sieve 、 camphor-10-sulfonic acid 作用下， 以 乙腈 为溶剂， 反应 0.92h， 生成 N⁶-Hexyl-2',3',5'-tri-O-benzoyladenosine
  参考文献：
  名称：

  Pentenyl ribosides: new reagents for purine nucleoside synthesis

  摘要：

  Protected pent-4-enyl ribosides and deoxyribosides were synthesized as reagents for the preparation of nucleosides and deoxynucleosides. Reaction of pent-4-enyl 2',3',5'-tri-O-benzoyl-D-erythro-pentofuranoside with five nucleobases in the presence of N-iodosuccinimide/trifluoromethanesulfonic acid (NIS/TfOH) produced the N-9-beta-nucleosides in 50-70% yields. Pent-4-enyl-2-deoxy-3',5'-di-O-p-toluyl-alpha-D-erythro-pentofuranoside coupled with 6-chloropurine in the presence of iodonium dicollidine perchlorate (IDCP) to produce a mixture of deoxynucleoside isomers (N-9, N-7, alpha,beta) in 91% yield. Under the same conditions, coupling of 6-chloropurine with pent-4-enyl 2'-deoxy-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-D-erythro-pentofuranoside produced only N-9alpha and N-9beta products in 40% total yield. The N-9beta nucleoside was the only product of the reaction of 6-chloropurine with pent-4-enyl 2'-O-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-D-erythro-pentofuranoside in the presence of NIS/TfOH. Pent-4-enyl ribosides appear to be useful reagents for the synthesis of ribo- and deoxyribonucleosides under mild (NIS/TfOH) or neutral (IDCP) conditions.

  DOI：

  10.1021/jo00077a057

文献信息

• Pentenyl ribosides: new reagents for purine nucleoside synthesis
  作者：Marie Christine Chapeau、Lawrence J. Marnett

  DOI：10.1021/jo00077a057

  日期：1993.12

  Protected pent-4-enyl ribosides and deoxyribosides were synthesized as reagents for the preparation of nucleosides and deoxynucleosides. Reaction of pent-4-enyl 2',3',5'-tri-O-benzoyl-D-erythro-pentofuranoside with five nucleobases in the presence of N-iodosuccinimide/trifluoromethanesulfonic acid (NIS/TfOH) produced the N-9-beta-nucleosides in 50-70% yields. Pent-4-enyl-2-deoxy-3',5'-di-O-p-toluyl-alpha-D-erythro-pentofuranoside coupled with 6-chloropurine in the presence of iodonium dicollidine perchlorate (IDCP) to produce a mixture of deoxynucleoside isomers (N-9, N-7, alpha,beta) in 91% yield. Under the same conditions, coupling of 6-chloropurine with pent-4-enyl 2'-deoxy-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-D-erythro-pentofuranoside produced only N-9alpha and N-9beta products in 40% total yield. The N-9beta nucleoside was the only product of the reaction of 6-chloropurine with pent-4-enyl 2'-O-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-D-erythro-pentofuranoside in the presence of NIS/TfOH. Pent-4-enyl ribosides appear to be useful reagents for the synthesis of ribo- and deoxyribonucleosides under mild (NIS/TfOH) or neutral (IDCP) conditions.