6-Chloro-9-(2'-deoxy-3',5'-di-O-p-toluyl-α-D-erythro-pentofuranosyl)purine | 139244-01-2

• 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: 6-Chloro-9-(2'-deoxy-3',5'-di-O-p-toluyl-α-D-erythro-pentofuranosyl)purine
• 英文别名: 6-chloro-9-(2-deoxy-3,5-di-O-toluoyl-β-D-erythro-pentofuranosyl)purine；6-chloro-α-2'-deoxy-3',5'-di-O-p-toluoylribofuranosylpurine；6-chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-B-D-erythro pentofuranosyl)purine；(2R,3S,5S)-5-(6-Chloro-9H-purin-9-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate；[(2R,3S,5S)-5-(6-chloropurin-9-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 139244-01-2
• 化学式: C₂₆H₂₃ClN₄O₅
• 分子量: 506.945
• InChiKey: NSOAHTMBUMXVAF-HBMCJLEFSA-N

物化性质

• 沸点：
  684.5±65.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-Chloro-9-(2'-deoxy-3',5'-di-O-p-toluyl-α-D-erythro-pentofuranosyl)purine 在 三甲基氯硅烷 、 1,1-二溴乙烷 、 sodium methylate 、 锌 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 57.0h， 生成
  参考文献：
  名称：

  高效合成6-（羟甲基）嘌呤。

  摘要：

  [反应：见正文]基于6-卤尿烷与酰氧基甲基锌碘化物的钯催化交叉偶联反应，然后脱保护，开发了一种简便而有效的合成6-（羟甲基）嘌呤衍生物（碱和核苷）的方法。几种标题化合物是腺苷脱氨酶的抑制剂，并具有抑制细胞生长的活性。

  DOI：

  10.1021/ol049059r
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 iodonium di(2,4,6-trimethylpyridine) perchlorate 吡啶 、 4 A molecular sieve 、 camphor-10-sulfonic acid 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 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

文献信息

• Facile Stereospecific Synthesis of a-Anomeric 2'-Deoxynucleosides
  作者：Kazuo Shinozuka、Yoshiki Hirota、Tsutomu Morita、Hiroaki Sawai

  DOI：10.3987/com-92-6125

  日期：——

  The coupling reaction of activated nucleobases, such as the sodium salts of N-benzoyladenine and 6-chloropurine and 2,4-bis-O-trimethylsilylthymine, with 1-alpha-chloro-2-deoxy-3,5-di-O-p-toluoylribofuranose (1) in a mixture of acetonitrile and tetrahydrufuran leads to the stereospecific formation of a-anomeric 2'-deoxynucleosides with satisfactory yields. The ratio of the distribution between the resulted alpha- and beta-stereoisomers was about 3:1 in each case. The method is simple and applicable to the preparation of both purine and pyrimidine alpha-2'-deoxynucleosides.
• Method for the production of 2'-deoxyadenosine compounds
  申请人：BRIGHAM YOUNG UNIVERSITY

  公开号：EP0173059B1

  公开（公告）日：1989-11-29
• US4760137A
  申请人：——

  公开号：US4760137A

  公开（公告）日：1988-07-26
• US5681941A
  申请人：——

  公开号：US5681941A

  公开（公告）日：1997-10-28
• US5811534A
  申请人：——

  公开号：US5811534A

  公开（公告）日：1998-09-22