8,2'-anhydro-8-oxy-(3,5-di-O-tetrahydropyran-2-yl-β-D-arabinofuranosyl)adenine | 62729-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 8,2'-anhydro-8-oxy-(3,5-di-O-tetrahydropyran-2-yl-β-D-arabinofuranosyl)adenine
• 英文别名: (6aS)-7c-(Ξ)-tetrahydropyran-2-yloxy-8t-(Ξ)-tetrahydropyran-2-yloxymethyl-(6ar,9ac)-6a,7,8,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-e]purin-4-ylamine；O^3',O^5'-(Ξ,Ξ)-bis-tetrahydropyran-2-yl-arabino-8,O^2'-cyclo-adenosine；3',5',O-Tetrahydropyranyl-8,2'-O-cycloadenosin；(11S,12R,13R,15R)-12-(oxan-2-yloxy)-13-(oxan-2-yloxymethyl)-10,14-dioxa-1,3,5,8-tetrazatetracyclo[7.6.0.02,7.011,15]pentadeca-2,4,6,8-tetraen-6-amine
• CAS: 62729-15-1
• 化学式: C₂₀H₂₇N₅O₆
• 分子量: 433.464
• InChiKey: COGWYXABVQVVHE-WWPIUETNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  8-溴膘苷 在 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 氨 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 8,2'-anhydro-8-oxy-(3,5-di-O-tetrahydropyran-2-yl-β-D-arabinofuranosyl)adenine
  参考文献：
  名称：

  Synthesis of 8-Substituted Analogues of 2′-Deoxy-2′-Fluoroadenosine

  摘要：

  After 3',5'-di-O-protection of 8-bromoadenosine, the product was converted to the arabinoside, which was successively treated with diethylaminosulfur trifluoride (DAST) and acid to afford 8-bromo-2'-deoxy-2'-fluoroadenosine. However, the formation of an 8,2'-anhydro compound was noted by treatment of the arabinoside with alkali. Finally, the 8-oxo analog was obtained from the 8-bromo congener.

  DOI：

  10.1080/07328319908044618

文献信息

• Studies of nucleosides and nucleotides—LXXIV
  作者：Morio Ikehara、Tokumi Maruyama、Hiroko Miki

  DOI：10.1016/0040-4020(78)80136-7

  日期：1978.1

  8,2'-O-Cycloadenosine was protected at 3' and 5'-OHs with acetyl groups and cleaved using liq. H2S. Subsequent dethiolation and mesylation gave 2'-O-mesyl-3',5'-di-O-acetyl-arabinosyladenine (6). When 6 or its deacetylated parent compound (7) was heated with sodium azide in DMF, 3'-azido-3'-deoxyxylofuranosyladenine (9) was the only product. The cyclonucleoside was then protected with tetrahydropyranyl

  将8，2′-O-环腺苷在3′和5′-OH处用乙酰基保护，并用Liq裂解。ħ 2 S.随后dethiolation和甲磺酰化，得到2'-O-甲磺酰基-3' ，5'-二-O-乙酰基阿拉伯糖腺嘌呤（6）。当6或它的脱乙酰化母体化合物（7）与在DMF中的叠氮化钠加热，3'-叠氮基-3'- deoxyxylofuranosyladenine（9）是唯一的产物。然后将环核苷用四氢吡喃基保护，并进行与上述相似的一系列反应，得到2'-O-甲磺酰基-3'，5'-二-O-四氢吡喃基阿拉伯糖基腺嘌呤（14）。将化合物14与叠氮化钠一起加热，然后进行酸性脱保护得到2'-叠氮基-2'16）。16的氢化得到2'-氨基-2'-脱氧腺苷（18）。通过用氯化锂处理14并随后脱保护，也获得了2'-Chloro-2'-脱氧腺苷（19）。描述了这些化合物的UV，IR和NMR光谱数据。
• Synthesis of 8-Substituted Analogues of 2′-Deoxy-2′-Fluoroadenosine
  作者：Tokumi Maruyama、Shigetada Kozai、Takako Manabe、Yuko Yazima、Yoshiko Satoh、Hiroshi Takaku

  DOI：10.1080/07328319908044618

  日期：1999.11

  After 3',5'-di-O-protection of 8-bromoadenosine, the product was converted to the arabinoside, which was successively treated with diethylaminosulfur trifluoride (DAST) and acid to afford 8-bromo-2'-deoxy-2'-fluoroadenosine. However, the formation of an 8,2'-anhydro compound was noted by treatment of the arabinoside with alkali. Finally, the 8-oxo analog was obtained from the 8-bromo congener.