Pent-4-enyl 2'-deoxy-3',5'-di-O-p-toluyl-α-D-erythro-pentofuranoside | 152279-05-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Pent-4-enyl 2'-deoxy-3',5'-di-O-p-toluyl-α-D-erythro-pentofuranoside
• CAS: 152279-05-5
• 化学式: C₂₆H₃₀O₆
• 分子量: 438.521
• InChiKey: WYIPFSMLYARRQU-VXNXHJTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-氯嘌呤 、 Pent-4-enyl 2'-deoxy-3',5'-di-O-p-toluyl-α-D-erythro-pentofuranoside 在 iodonium di(2,4,6-trimethylpyridine) perchlorate 4 A molecular sieve 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以17%的产率得到6-Chloro-9-(2'-deoxy-3',5'-di-O-p-toluyl-α-D-erythro-pentofuranosyl)purine
  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
• 作为产物：
  描述：

  4-戊烯-1-醇 在 吡啶 、 camphor-10-sulfonic acid 作用下， 生成 Pent-4-enyl 2'-deoxy-3',5'-di-O-p-toluyl-α-D-erythro-pentofuranoside
  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