3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-8-mercaptoadenosine | 208402-30-6

• 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: 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-8-mercaptoadenosine
• 英文别名: 9-[(6aR,8R,9R,9aS)-9-hydroxy-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-6-amino-7H-purine-8-thione
• CAS: 208402-30-6
• 化学式: C₂₂H₃₉N₅O₅SSi₂
• 分子量: 541.819
• InChiKey: SOBCLJSMTHZTBB-QTQZEZTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  156
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-8-mercaptoadenosine 在 四丁基氟化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 49.0h， 生成 8,2'-S-cyclo-adenosine
  参考文献：
  名称：

  Facile Synthesis of 8, 2′-S-Cyclopurine Nucleoside

  摘要：

  This paper describes the synthesis of 8,2'-anhydro-8-mercapto-9-(beta-D-arabinofuranosyl)purine (8,2'-S-cyclopurinenucleoside, 1) via the shorter route from 3',5'-di-O-acectyl-8,2'-S-cycloadenosine (6) and by direct reductive deamination with n-pentyl nitrite in tetrahydrofuran (THF) and deacetylation. The preparation of 8,2'-S-cycloadenosine (2) was achieved in good yield by the cyclization of the protected 8-mercaptoadenosine with triphenylphosphine and diethyl azodicarboxylate (DEAD) in THF at room temperature, under Mitsunobu reaction conditions.

  DOI：

  10.1080/07328319808003459
• 作为产物：
  描述：

  8-mercaptoadenosine 、 1,3二氯-1,1,3,3-四异丙基二硅氧烷 在 吡啶 作用下， 反应 1.0h， 以66%的产率得到3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-8-mercaptoadenosine
  参考文献：
  名称：

  Facile Synthesis of 8, 2′-S-Cyclopurine Nucleoside

  摘要：

  This paper describes the synthesis of 8,2'-anhydro-8-mercapto-9-(beta-D-arabinofuranosyl)purine (8,2'-S-cyclopurinenucleoside, 1) via the shorter route from 3',5'-di-O-acectyl-8,2'-S-cycloadenosine (6) and by direct reductive deamination with n-pentyl nitrite in tetrahydrofuran (THF) and deacetylation. The preparation of 8,2'-S-cycloadenosine (2) was achieved in good yield by the cyclization of the protected 8-mercaptoadenosine with triphenylphosphine and diethyl azodicarboxylate (DEAD) in THF at room temperature, under Mitsunobu reaction conditions.

  DOI：

  10.1080/07328319808003459

文献信息

• Facile Synthesis of 8, 2′-<i>S</i>-Cyclopurine Nucleoside
  作者：Keiko Tekenaka、Tadakazu Tsuji、Masako Muraoka

  DOI：10.1080/07328319808003459

  日期：1998.5

  This paper describes the synthesis of 8,2'-anhydro-8-mercapto-9-(beta-D-arabinofuranosyl)purine (8,2'-S-cyclopurinenucleoside, 1) via the shorter route from 3',5'-di-O-acectyl-8,2'-S-cycloadenosine (6) and by direct reductive deamination with n-pentyl nitrite in tetrahydrofuran (THF) and deacetylation. The preparation of 8,2'-S-cycloadenosine (2) was achieved in good yield by the cyclization of the protected 8-mercaptoadenosine with triphenylphosphine and diethyl azodicarboxylate (DEAD) in THF at room temperature, under Mitsunobu reaction conditions.