2',5'-di-O-acetyl-3'-deoxyinosine | 204978-87-0

• 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: 2',5'-di-O-acetyl-3'-deoxyinosine
• 英文别名: 3'-Deoxyinosine 2',5'-Diacetate；[(2S,4R,5R)-4-acetyloxy-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 204978-87-0
• 化学式: C₁₄H₁₆N₄O₆
• 分子量: 336.304
• InChiKey: ZAXARJNUAPVWGP-IMSIIYSGSA-N

物化性质

• 熔点：
  242-244 °C
• 沸点：
  626.5±55.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2',5'-di-O-acetyl-3'-deoxyinosine 在 ammonium hydroxide 、 potassium dihydrogenphosphate 、 recombinant E_. coli purine nucleoside phosphorylase 作用下， 以 甲醇 、 水 为溶剂， 反应 289.0h， 生成 肌苷
  参考文献：
  名称：

  化学合成2-氯和2-氟代吡啶二酮

  摘要：

  摘要 两种方法的2-fluorocordycepin和2- chlorocordycepin的酶法合成进行了研究：（i）使用的3'-脱氧腺苷（虫草素）和3'-脱氧肌苷（3'dIno）为3-脱氧供体d -ribofuranose重组大肠杆菌嘌呤核苷磷酸化酶（PNP）催化2-氟-（2F Ade）和2-氯腺嘌呤（2Cl Ade）的糖基转移，以及（ii）使用2-氟腺苷和3'-脱氧肌苷交叉糖基化的底物和PNP作为生物催化剂。开发了一种从肌苷开始合成3'-脱氧肌苷的有效方法。但是，2Cl Ade和2F的溶解度非常差Ade是第一种方法的限制因素。第二种方法能够克服这个问题，并且从实际合成标题核苷的角度来看，它比前一种方法更具优势。发现通过PNP在3'dIno磷酸分解中形成的3-deoxy-α- d-呋喃呋喃糖-1-磷酸中间体分别是大肠杆菌胸苷（TP）和尿苷（UP）磷酸化酶的弱底物和边缘底物。最后，一锅煮级联变换3-脱氧d

  DOI：

  10.1055/s-0036-1590804
• 作为产物：
  描述：

  肌苷 在 偶氮二异丁腈 、 三正丁基氢锡 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 11.0h， 生成 2',5'-di-O-acetyl-3'-deoxyinosine
  参考文献：
  名称：

  经由嘌呤3'-脱氧核苷合成9-（2,3-二脱氧-2-氟-β-D-苏-戊呋喃糖基）腺嘌呤（FddA）。

  摘要：

  经由6-氯-9-（3-脱氧-β-D-赤型-五氟呋喃糖基）合成9-（2,3-二脱氧-2-氟-β-D-苏-五呋喃糖基）腺嘌呤（1，FddA）描述了易于从肌苷（5）获得的）-9H-嘌呤（9）。通过引入6-氯基团可以改善嘌呤3'-脱氧核苷的C2'-β位置与三乙二氨基氨基硫的氟化作用，并且产率中等。嘌呤3'-脱氧核苷衍生物也与三乙胺三氟化氢进行亲核反应，并以良好的收率得到所需的氟化核苷。通过使用三乙胺三氟化氢大大提高了氟化工艺的安全性和产率。

  DOI：

  10.1021/jo0158985

文献信息

• Methods for producing nucleoside derivatives and intermediates therefor
  申请人：Ajinomoto Co., Inc.

  公开号：US06090937A1

  公开（公告）日：2000-07-18

  Novel intermediates of nucleoside derivatives, of which the 6-position of the nucleic acid base moiety is substituted with a halogen atom, are produced. Using those novel intermediates, even substrates, of which the 3'-position of the saccharide moiety is deoxylated, can be substituted at the 2'-position at an extremely high yield. Specifically, by subjecting a 3'-deoxy derivative of inosine to 6-halogenation to give a 6-halide of the derivative, and then subjecting it to 2'-deoxylation/substitution with a fluorine atom or the like, followed by further subjecting it to substitution with an amino group, a hydroxyl group or any other intended substituent at the 6-positioned halogen atom, nucleoside derivatives are produced at a high yield. Methods for producing nucleoside derivatives including 9-(2,3-dideoxy-2-fluoro-.beta.-D-threo-pentofuranosyl)adenine (FddA) and their related compounds, in a simplified manner, at a high yield and at low costs, and especially Economical methods for substituting substrates, of which the 3'-position of the saccharide moiety is deoxylated, at the 2'-position to produce those nucleoside derivatives on an industrial scale are also provided.

  生产新型核苷衍生物的中间体，其中核酸碱基部分的6位被卤素原子取代。利用这些新型中间体，即使脱氧糖苷部分的3'-位也可以以极高的产率在2'-位进行取代。具体来说，通过将肌苷的3'-脱氧衍生物经过6-卤化处理，得到该衍生物的6-卤化物，然后进行2'-脱氧化/以氟原子等进行取代，随后进一步进行6-位卤素原子处的氨基团、羟基或其他取代基的取代，可以高产率地生产核苷衍生物。提供了一种简化方式、高产率、低成本地生产包括9-(2,3-脱氧-2-氟-β-D-巯基-戊呋糖基)腺嘌呤（FddA）及其相关化合物的核苷衍生物的方法，特别是提供了一种经济的方法，用于在工业规模上取代脱氧糖苷部分的3'-位以在2'-位生产这些核苷衍生物。
• PROCESS FOR PRODUCING NUCLEIC ACID DERIVATIVES
  申请人：——

  公开号：US20020045744A1

  公开（公告）日：2002-04-18

  There can be provided an excellent industrial process for producing compounds having sugar-moiety hydroxyl groups or halogen atoms reduced in nucleic acids or in derivatives thereof by allowing O-thiocarbonyl derivatives of sugar-moiety hydroxyl groups or allowing halogenated derivatives in the sugar-moiety, in the nucleic acids or in derivatives thereof to react with any one of hypophosphorous acids (including salts thereof) and phosphites (esters) which are inexpensive, non-toxic and safely usable as radical reducing agents in industrial scale, in the presence of a radical reaction initiator. The process of the present invention is an industrially useful and highly safe process for reducing sugar-moiety hydroxyl groups and halogen atoms in nucleic acids or derivatives thereof (including nucleic acid-related compounds) at low costs.

  可以提供一个出色的工业过程，用于通过允许具有糖基羟基或卤原子的化合物在核酸或其衍生物中减少，通过允许糖基羟基的O-硫酰衍生物或在核酸中或其衍生物中允许卤代衍生物与任何一种廉价、无毒且安全可用作工业规模中的自由基还原剂的次磷酸（包括其盐）和磷酸酯（酯）反应，在自由基反应引发剂的存在下。本发明的工艺是一种在低成本下减少核酸或其衍生物（包括核酸相关化合物）中的糖基羟基和卤原子的工业上有用且高度安全的过程。
• Methods for producing nucleoside derivatives and intermediates therefore
  申请人：Ajinomoto Co., Inc.

  公开号：EP0945460A1

  公开（公告）日：1999-09-29

  Novel intermediates of nucleoside derivatives, of which the 6-position of the nucleic acid base moiety is substituted with a halogen atom, are produced. Using those novel intermediates, even substrates, of which the 3'-position of the saccharide moiety is deoxylated, can be substituted at the 2'-position at an extremely high yield. Specifically, by subjecting a 3'-deoxy derivative of inosine to 6-halogenation to give a 6-halide of the derivative, and then subjecting it to 2'-deoxylation/substitution with a fluorine atom or the like, followed by further subjecting it to substitution with an amino group, a hydroxyl group or any other intended substituent at the 6-positioned halogen atom, nucleoside derivatives are produced at a high yield. Methods for producing nucleoside derivatives including 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (FddA) and their related compounds, in a simplified manner, at a high yield and at low costs , and especially Economical methods for substituting substrates, of which the 3'-position of the saccharide moiety is deoxylated, at the 2'-position to produce those nucleoside derivatives on an industrial scale are also provided.

  生产出了核苷衍生物的新型中间体，其中核酸碱基的 6 位被卤原子取代。利用这些新型中间体，即使是糖基的 3'- 位被脱氧的底物，也能以极高的产率在 2'- 位被取代。具体来说，将肌苷的 3'-脱氧衍生物进行 6-卤化，得到该衍生物的 6-卤化物，然后将其进行 2'-脱氧/与氟原子或类似物进行取代，再将其与氨基、羟基或 6-位卤原子上的任何其他预期取代基进行取代，就能以高产率生产出核苷衍生物。 本发明还提供了以简化的方式、高产率和低成本生产核苷衍生物（包括 9-(2,3-二脱氧-2-氟-β-D-三呋喃戊糖基)腺嘌呤 (FddA)及其相关化合物）的方法，特别是在 2'-位上取代糖基 3'-位脱氧的底物以工业规模生产这些核苷衍生物的经济方法。
• Process for producing nucleoside derivatives
  申请人：Ajinomoto Co., Inc.

  公开号：EP0999218A1

  公开（公告）日：2000-05-10

  An industrially applicable process is provided for producing nucleic acids or derivatives thereof having their sugar-moiety hydroxyl groups or halogen atoms reduced. According to this process, O-thiocarbonyl derivates of the sugar-moiety hydroxyl groups or derivatives halogenated in the sugar-moiety, are allowed to react, in the presence of a radical reaction initiator, with any one of hypophosphorous acids (including salts thereof) and phosphites (esters) which are inexpensive, non-toxic and safely usable as radical reducing agents on an industrial scale. The process of the present invention is an industrially useful and highly safe process for reducing sugar-moiety hydroxyl groups and halogen atoms in nucleic acids or derivatives thereof (including nucleic acid-related compounds) at low costs.

  本发明提供了一种工业上适用的工艺，用于生产糖分子羟基或卤素原子被还原的核酸或其衍生物。 根据该工艺，糖分子羟基的 O-硫代羰基衍生物或糖分子中卤化的衍生物，在自由基反应引发剂的存在下，可与任何一种次磷酸（包括其盐）和亚磷酸酯（酯）发生反应，次磷酸和亚磷酸酯价格低廉、无毒，可安全地用作工业规模的自由基还原剂。 本发明的工艺是一种工业上有用且高度安全的工艺，可以低成本还原核酸或其衍生物（包括核酸相关化合物）中的糖分子羟基和卤素原子。
• An Industrial Process for Synthesizing Lodenosine (FddA)
  作者：Kunisuke Izawa、Satoshi Takamatsu、Satoshi Katayama、Naoko Hirose、Shigetaka Kozai、Tokumi Maruyama

  DOI：10.1081/ncn-120021951

  日期：2003.10

  Two industrial synthetic approaches to Lodenosine (1, FddA, 9-(2,3-dideoxy-2-fluoro-p-D-threo-pentofuranosyl) adenine) via a purine riboside or a purine 3'-deoxyriboside are described. Several novel applications of deoxygenation and fluorination methods are compared considering reaction yields, economy, safety and environmental concerns.