环阿拉伯糖基腺嘌呤 | 13089-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 环阿拉伯糖基腺嘌呤
• 英文名称: 8,2'-anhydro-8-oxy-9-β-D-arabinofuranosyladenine
• 英文别名: (6aS)-4-amino-8t-hydroxymethyl-(6ar,9ac)-6a,7,8,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-e]purin-7c-ol；arabino-8,O^2'-cyclo-adenosine；8,2'-Anhydro-8-hydroxy-(9β-D-arabinofuranosyl)-adenin；8,2'-Anhydro-8-hydroxy-9-β-D-arabino-furanosyladenin；8,2'-Anhydro-8-hydroxy-9β-D-arabinofuranosyl-adenin；8,2'-O-Anhydro(9-ss-D-arabinofuranosyl)-8-hydroxyadenin；Carbocyclic arabinosyladenine；(11S,12R,13R,15R)-6-amino-13-(hydroxymethyl)-10,14-dioxa-1,3,5,8-tetrazatetracyclo[7.6.0.02,7.011,15]pentadeca-2,4,6,8-tetraen-12-ol
• CAS: 13089-44-6
• 化学式: C₁₀H₁₁N₅O₄
• 分子量: 265.228
• InChiKey: MQMVTEZRMYGLFD-FJFJXFQQSA-N

物化性质

• 沸点：
  647.0±65.0 °C(Predicted)
• 密度：
  2.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  环阿拉伯糖基腺嘌呤 在 吡啶 、 sodium hydrogensulfide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 8,5'-Anhydro-8-mercapto-9-β-D-arabinofuranosyladenin
  参考文献：
  名称：

  Studies of nucleosides and nucleotides. LX. Purine cyclonuclesides. (22). Synthesis of 8,5'-anhydro-8-mercapto-9-.BETA.-D-xylofuranosyladenine by the rearrangement of O-cyclonucleosides.

  摘要：

  8.2-脱水-9-β-D-阿拉伯呋喃糖基腺嘌呤（I）转化为5'-对甲苯磺酰基衍生物（II），产率为75%。当化合物（II）与硫化氢钠在二甲基甲酰胺（DMF）中加热时，得到具有阿拉伯糖构型的5'-S-环核苷（IV），产率为46%。从二对甲苯磺酰基衍生物（III）中类似地得到具有3'-对甲苯磺酰基的环核苷（VII）。8, 3'-脱水-9-β-D-木糖呋喃糖基腺嘌呤（VIII）转化为5'-对甲苯磺酰基衍生物（IX），并与硫化氢钠在DMF中加热。除了具有木糖呋喃糖构型的8, 5-S-环核苷（X）外，还得到两种化合物，即8, 3'-脱水-8-氧-9-(5'-脱氧-5'-巯基-β-D-木糖呋喃糖基)腺嘌呤二硫醚（XI）和5'-脱氧-5'-巯基-8-氧-9-β-D-木糖呋喃糖

  DOI：

  10.1248/cpb.23.1114
• 作为产物：
  描述：

  阿糖腺苷 在 盐酸 、 silica gel 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 1.5h， 生成 环阿拉伯糖基腺嘌呤
  参考文献：
  名称：

  New procedure for the chlorination of pyrimidine and purine nucleosides

  摘要：

  DOI：

  10.1021/jo00326a053

文献信息

• Studies of nucleosides and nucleotides—LIV
  作者：M. Ikehara、Y. Ogiso

  DOI：10.1016/s0040-4020(01)93816-5

  日期：1972.1

  Reaction of 8,2′-anhydro-8-oxy-9-β-d-arabinofuranosyladenine (I) with various nucleophiles is reported. I reacts with liquid ammonia to give 8-amino-9-β-d-arabinofuranosyladenine (IV) and 8,5′-anhydro-8-oxy-9-β-d-arabinofuranosy (VI). The latter is also obtained by heating I at 60° in 0·01 N sodium hydroxide with which it is in equilibrium.

  报道了8，2′-脱水-8-氧基-9-β-呋喃糖基丝氨酸腺嘌呤（I）与各种亲核试剂的反应。我与液态氨反应生成8-氨基-9-β-d-阿拉伯呋喃糖基腺嘌呤（IV）和8,5'-脱水8-氧基-9-β-d-阿拉伯呋喃糖基（VI）。后者也可以通过在0°01 N的氢氧化钠中将I在60°加热使其平衡来获得。
• 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。
• Polynucleotides. XXIV. Synthesis and properties of a dinucleoside monophosphate derived from 8,2'-O-cycloadenosine
  作者：Morio Ikehara、Seiichi Uesugi、Junichi Yano

  DOI：10.1021/ja00822a040

  日期：1974.7
• New procedure for the chlorination of pyrimidine and purine nucleosides
  作者：Eung K. Ryu、Malcolm MacCoss

  DOI：10.1021/jo00326a053

  日期：1981.6
• Studies of nucleosides and nucleotides. LX. Purine cyclonuclesides. (22). Synthesis of 8,5'-anhydro-8-mercapto-9-.BETA.-D-xylofuranosyladenine by the rearrangement of O-cyclonucleosides.
  作者：MORIO IKEHARA、YUKO OGISO

  DOI：10.1248/cpb.23.1114

  日期：——

  8.2-Anhydro-9-β-D-arabinofuranosyladenine (I) was converted to 5'-tosyl derivative (II) in a yield of 75%. When Compound (II) was heated with sodium hydrogen sulfide in dimethylformamide (DMF) 8, 5'-S-cyclonucleoside having arabinosyl configuration (IV) was obtained in a yield of 46%. From the ditosyl derivative (III) analogously a cyclonucleoside having 3'-tosyl group (VII) was obtained. 8, 3'-Anhydro-9-β-D-xylofuranosyladenine (VIII) was converted to 5'-tosyl derivative (IX) and heated with sodium hydrogensulfide in DMF. In addition to a 8, 5-S-cyclonucleoside of xylofuranosyl configuration (X), two compounds, 8, 3'-anhydro-8-oxy-9-(5'-deoxy-5'-mercapto-β-D-xylofuranosyl) adenine disulfide (XI) and 5'-deoxy-5'-mercapto-8-oxy-9-β-D-xylofuranosyladenine (XII) was obtained. Compound (XII) was also obtained from X by the treatment with 0.01N sodium hydroxide. Thus, the OH group of xylo configuration in the sugar moiety of 8, 5'-S-cyclonucleoside was found to be able to cleave the S-hydro linkage even in a mild condition.

  8.2-脱水-9-β-D-阿拉伯呋喃糖基腺嘌呤（I）转化为5'-对甲苯磺酰基衍生物（II），产率为75%。当化合物（II）与硫化氢钠在二甲基甲酰胺（DMF）中加热时，得到具有阿拉伯糖构型的5'-S-环核苷（IV），产率为46%。从二对甲苯磺酰基衍生物（III）中类似地得到具有3'-对甲苯磺酰基的环核苷（VII）。8, 3'-脱水-9-β-D-木糖呋喃糖基腺嘌呤（VIII）转化为5'-对甲苯磺酰基衍生物（IX），并与硫化氢钠在DMF中加热。除了具有木糖呋喃糖构型的8, 5-S-环核苷（X）外，还得到两种化合物，即8, 3'-脱水-8-氧-9-(5'-脱氧-5'-巯基-β-D-木糖呋喃糖基)腺嘌呤二硫醚（XI）和5'-脱氧-5'-巯基-8-氧-9-β-D-木糖呋喃糖