8,2'-anhydro-8-mercaptoguanosine | 37070-11-4

• 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-mercaptoguanosine
• 英文别名: 8,2'-S-cycloguanosine；(6aS)-2-amino-7c-hydroxy-8t-hydroxymethyl-(6ar,9ac)-6a,7,8,9a-tetrahydro-3H-furo[2',3':4,5]thiazolo[3,2-e]purin-4-one；8,2'-sulfanediyl-arabino-2'-deoxy-guanosine；8,2'-anhydro-8-mercapto-9-β-arabinofuranosylguanine；8,2'-anhydro-8-mercapto-9-b-D-arabinofuranosylguanine；8,2'-Thioanhydroguanosin；(11S,12R,13R,15R)-4-amino-12-hydroxy-13-(hydroxymethyl)-14-oxa-10-thia-1,3,5,8-tetrazatetracyclo[7.6.0.02,7.011,15]pentadeca-2(7),3,8-trien-6-one
• CAS: 37070-11-4
• 化学式: C₁₀H₁₁N₅O₄S
• 分子量: 297.294
• InChiKey: GIJNDJWONIVREX-AJFJRRQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  20
• 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：
  160
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8,2'-anhydro-8-mercaptoguanosine 在 nickel-aluminum alloy sodium hydroxide 、 水 作用下， 反应 15.0h， 以44%的产率得到2'-脱氧鸟苷
  参考文献：
  名称：

  Production method of 2'-deoxyguanosine compound

  摘要：

  本发明提供了一种通过在溶剂中在碱的存在下使用镍或镍合金对以下式（1）表示的8,2'-脱硫-8-巯基-9-β-阿拉伯呋喃核苷鸟嘌呤化合物进行脱硫反应的生产方法，从而得到以下式（2）表示的2'-去氧鸟苷化合物。其中R1、R2、R4和R5分别独立地是氢原子或羟基保护基，R3和R6是氢原子或氨基保护基。

  公开号：

  EP1683806A1
• 作为产物：
  描述：

  8-巯基鸟苷 在 吡啶 、 四丁基氟化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 23.17h， 生成 8,2'-anhydro-8-mercaptoguanosine
  参考文献：
  名称：

  Nucleosides VI: A Novel and Convenient Synthesis of PurineS-Cyclonucleosides Via Mitsunobu Reaction

  摘要：

  Two representative S-cyclonucleosides, 8,5'-anhydro-2', 3'-O-isopropylidene-8-mercaptoadenosine (3) and 8,2'-anhydro-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-8-mercaptoguanosine (8), were prepared in good yields by dropwise addition of one equivalent each of triphenylphosphine and DEAD in DMF into a mixture of 2',3'-O-isopropylidene-8-mercaptoadenosine (2) or 3',5'-O-(tetra-iso-propyldisiloxane-1,3-diyl)-8-mercaptoguanosine (7), respectively, in DMF. Treatment of compound 2 with two equivalents each of triphenylphosphine and DEAD in DMF afforded N-[8,5'-anhydro-2',3'-0-isopropylidene-8-mercaptopurin-6-yl]triphenylphospha-lambda5-azene (4) in 87% yield.

  DOI：

  10.1080/07328319308018564

文献信息

• Production method of fluorinated purine nucleoside derivative, intermediate therefor and production method thereof
  申请人：Ajinomoto Co., Inc.

  公开号：EP1816135A1

  公开（公告）日：2007-08-08

  Purine nucleosides which are fluorinated at the 3'-position (preferably the α-position), may be economically and efficiently produced by fluorinating a novel purine nucleoside derivative (1) in which the hydroxyl group at the 5'-position is protected to obtain a novel purine nucleoside derivative (2) in a high yield. The derivative (2) is subjected to desulfurization, deprotection of R1 and, as necessary protection, deprotection, or modification of nucleic acid base moiety, to obtain the desired purine nucleoside (3). wherein each symbol is as defined in the specification.

  嘌呤核苷在3'-位（最好是α-位）被氟化后，可以通过氟化一种新的嘌呤核苷衍生物（1）来经济高效地生产，其中5'-位的羟基被保护以获得高产率的新嘌呤核苷衍生物（2）。衍生物（2）经过脱硫化、去保护R1，必要时保护、去保护或修饰核酸碱基部分，以获得所需的嘌呤核苷（3）。 其中每个符号的定义如规范中所述。
• Synthesis and properties of 2,6-diamino-8,2'-anhydro-8-mercapto-9-.BETA.-D-arabinofuranosylpurine.
  作者：MASAKO MURAOKA

  DOI：10.1248/cpb.29.3449

  日期：——

  2, 6-Diamino-9-β-D-ribofuranosylpurine (I) was brominated with saturated bromine-water to the 8-bromo compound (II), which was tosylated at the 2'-hydroxygroup via the 2', 3'-O-dibutylstannylene compound (III). The resulting 2, 6-diamino-8-bromo-9-(2'-O-tosyl-β-D-ribofuranosyl)-purine (IV) was cyclized with thiourea in n-propanol or 40% sodium hydrogen sulfide to give 2, 6-diamino-8, 2'-anhydro-8-mercapto-9-β-D-arabinofuranosylpurine (V) in yields of 40% and 80%, respectively. Alternatively, 8, 2'-anhydro-8-mercapto-9-β-D-arabinofuranosylguanine (VI) was acetylated and chlorinated with phosphoryl chloride to give the 2-amino-6-chloropurine-8, 2'-S-cyclonucleoside derivative (VIII), which was aminated with ammonia in methanol to afford the 2, 6-diaminopurine cyclonucleoside (V) in a yield of 45%. Catalytic desulfurization of the cyclonucleoside (V) gave 2, 6-diamino-9-(2'-deoxy-β-D-ribofuranosyl)-purine (IX). Some physical properties of these compounds were elucidated by ultraviolet (UV), nuclear magnetic resonance (NMR) and circular dichroism (CD) spectroscopy. The CD spectra of these nucleosides and cyclonucleoside were similar to those of the corresponding adenine nucleosides and cyclonucleoside in general.

  将 2，6-二氨基-9-β-D-呋喃核糖基嘌呤 (I) 用饱和溴水溴化，得到 8-溴化合物 (II)，再通过 2'，3'-O-二丁基亚锡化合物 (III) 在 2'-羟基上进行对甲苯基化。得到的 2，6-二氨基-8-溴-9-(2'-O-对甲苯磺酸-β-D-呋喃核糖基)-嘌呤 (IV) 在正丙醇或 40% 硫化氢钠中与硫脲环化，得到 2，6-二氨基-8，2'-脱水-8-巯基-9-β-D-阿拉伯呋喃糖基嘌呤 (V)，产率分别为 40% 和 80%。另外，将 8，2'-脱水-8-巯基-9-β-D-阿拉伯呋喃糖基鸟嘌呤（VI）乙酰化并用磷酰氯氯化，得到 2-氨基-6-氯嘌呤-8，2'-S-环核苷衍生物（VIII），该衍生物在甲醇中用氨进行胺化，得到 2，6-二氨基嘌呤环核苷（V），产率为 45%。对环核苷 (V) 进行催化脱硫，得到 2，6-二氨基-9-(2'-脱氧-β-D-呋喃核糖基)-嘌呤 (IX)。这些化合物的一些物理性质通过紫外线（UV）、核磁共振（NMR）和圆二色光谱（CD）得到了阐明。这些核苷和环核苷的 CD 光谱与相应的腺嘌呤核苷和环核苷的一般光谱相似。
• PROCESS FOR THE SYNTHESIS OF 2'-O-SUBSTITUTED PURINES
  申请人：Ravikumar Vasulinga

  公开号：US20080234475A1

  公开（公告）日：2008-09-25

  The present invention provides an improved process for the synthesis of 2′-O-substituted purine nucleosides. The process includes anhydro or thioanhydro ring opening of a selected 8,2′-cyclopurine nucleoside with a weak nucleophile in the presence of a Lewis acid ester, followed by reduction to afford the desired 2′-O-substituted purine nucleoside.

  本发明提供了一种改进的合成2'-O-取代嘌呤核苷的方法。该方法包括在路易斯酸酯的存在下，使用弱亲核试剂进行选择性的8,2'-环戊嘧啶核苷的无水或硫醇无水环开启，然后还原以得到所需的2'-O-取代嘌呤核苷。
• Synthesis of Nucleotides from 8,2′-Thioanhydropurine Nucleosides
  作者：Kelvin K. Ogilvie、Lewis A. Slotin

  DOI：10.1139/v73-359

  日期：1973.7.15

  The 5′-mono and diphosphates of the common 8,2′-thioanhydropurine nucleosides have been prepared and studied with 5′-nucleotidase. alkaline phosphatase, and adenylate kinase. Procedures for the preparation of protected anhydronucleosides and their incorporation into dianhydronucleoside monophosphates have been developed. These nucleotides have been found to be completely resistant to spleen and snake

  常见的 8,2'-硫代脱水嘌呤核苷的 5'-单磷酸酯和二磷酸酯已被制备并用 5'-核苷酸酶进行了研究。碱性磷酸酶和腺苷酸激酶。已开发出制备受保护的脱水核苷并将其掺入二脱水核苷单磷酸酯的方法。已发现这些核苷酸对脾脏和蛇毒磷酸二酯酶具有完全抗性，但很容易与雷尼镍一起转化为天然的 2'-脱氧核苷酸。
• A concise synthesis of 3′-α-fluoro-2′,3′-dideoxyguanosine (FddG) via 3′-α-selective fluorination of 8,2′-thioanhydronucleoside
  作者：Takayoshi Torii、Tomoyuki Onishi、Kunisuke Izawa、Tokumi Maruyama

  DOI：10.1016/j.tetlet.2006.06.074

  日期：2006.8

  The antiviral nucleoside 3'-alpha-fluoro-2',3'-dideoxyguanosine (FddG) was synthesized via 3'-alpha-selective fluorination of 8,2'thioanhydronucleoside as the key step. Desulfurization of Y-alpha-fluoro-3'-deoxy-8,2'-thioanhydronucleoside could be achieved by the treatment with Raney Ni in toluene. This method provides a concise route to 3'-alpha-fluoro-2',3'-dideoxynucleosides that avoids the use of explosive and expensive SF4-related fluorinating reagents. (c) 2006 Elsevier Ltd. All rights reserved.