1-<5'-O-(tert-butyldimethylsilyl)-3'-deoxy-β-D-glycero-pentofuranos-2'-ulosyl>uracil | 134100-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-<5'-O-(tert-butyldimethylsilyl)-3'-deoxy-β-D-glycero-pentofuranos-2'-ulosyl>uracil
• 英文别名: 1-((2R,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3-oxotetrahydrofuran-2-yl)pyrimidine2,4(1H,3H)-dione；5'-O-(t-Butyldimethylsilyl)-2',3'-dideoxy-2'-oxo-uridine；1-[(2R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-oxooxolan-2-yl]pyrimidine-2,4-dione
• CAS: 134100-06-4
• 化学式: C₁₅H₂₄N₂O₅Si
• 分子量: 340.451
• InChiKey: GFQSLODRIZOBLB-GXFFZTMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-<5'-O-(tert-butyldimethylsilyl)-3'-deoxy-β-D-glycero-pentofuranos-2'-ulosyl>uracil 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 4.5h， 生成 1-(2,3-dideoxy-2-C-methyl-β-D-threo-pentofuranosyl)uracil
  参考文献：
  名称：

  核苷和核苷酸。120.核苷糖部分中叔醇的立体选择性自由基脱氧：2'，3'-dideoxy-2'- C-甲基--2' - C-乙炔基-β-d-苏-戊呋喃糖基嘧啶和腺嘌呤作为潜在的抗病毒和抗肿瘤药物

  摘要：

  相应的3'-脱氧-2'- C-甲基-β-d-苏-戊呋喃糖基-嘧啶和-腺嘌呤的2'- O-甲氧基草酸酯的自由基脱氧，它们易于从1-（3）的反应中获得脱氧β-D-赤-pentofuran -2-酮糖基）嘧啶，并用的MeMgBr腺嘌呤衍生物，得到立体专一2'，3'-双脱氧-2'- ç甲基- β-D-苏式-pentofuranosyl -尿嘧啶（9A），脱保护后的-胸腺嘧啶（9b），-胞嘧啶（9c）和-腺嘌呤（18）。同样，合成2'，3'-二脱氧-2'- C-乙炔基-β-d-苏式通过相应的酮与LiCCTMS的反应，然后对叔-甲恶草酸酯进行自由基脱氧反应，可制得-呋喃呋喃糖基胸腺嘧啶（25）和-腺嘌呤（31）。描述了这些核苷在体外的细胞毒性和抗HIV活性。

  DOI：

  10.1016/s0040-4020(01)96259-3
• 作为产物：
  描述：

  2',5'-Bis-O-(tert-butyldimethylsilyl)-3'-deoxyuridine 在 吡啶 、 chromium(VI) oxide 、 四丁基氟化铵 作用下， 以 二氯甲烷 、 乙酸酐 为溶剂， 反应 3.0h， 生成 1-<5'-O-(tert-butyldimethylsilyl)-3'-deoxy-β-D-glycero-pentofuranos-2'-ulosyl>uracil
  参考文献：
  名称：

  Synthesis of 2′-C-cyano-2′-deoxy- and 2′-C-cyano-2′,3′-dideoxy-β-d-arabinofuranosyl nucleosides

  摘要：

  A series of 2'-C-cyano-2'-deoxy- and 2'-C-cyano-2',3'-dideoxy arabinofuranosyl nucleosides have been prepared by reaction of the corresponding 2'-ulosyl- and 3'-deoxy-2'-ulosyl nucleosides with sodium cyanide followed by 2'-deoxygenation of the cyanohyrins formed and removal of the protecting groups of the sugar moiety.

  DOI：

  10.1016/s0040-4020(01)88727-5

文献信息

• Analogs of oxetanyl purines and pyrimidines
  申请人：Abbott Laboratories

  公开号：US05597824A1

  公开（公告）日：1997-01-28

  A compound of the formula: ##STR1## wherein B is a purin-9-yl group or a heterocyclic isostere of a purin-9-yl group; or a pyrimidin-1-yl group or a heterocyclic isostere of a pyrimidin-1-yl group; A is --CH-- or A--G taken together is --C(.dbd.O)--, --C(.dbd.CH.sub.2)--, --C(OH)(CH.sub.2 OH)-- or ##STR2## and G and D are functional groups; or a pharmaceutically acceptable salt or ester thereof.

  该化合物的化学式为：##STR1## 其中B是嘌呤-9-基团或嘌呤-9-基团的杂环等价物；或嘧啶-1-基团或嘧啶-1-基团的杂环等价物；A是--CH--或A--G结合在一起是--C(.dbd.O)--、--C(.dbd.CH.sub.2)--、--C(OH)(CH.sub.2 OH)--或##STR2##，G和D是功能基团；或其药学上可接受的盐或酯。
• A Unified Strategy to Fluorinated Nucleoside Analogues <i>Via</i> an Electrophilic Manifold
  作者：Andrew J. Neel、Ben W. H. Turnbull、William P. Carson、Tamas Benkovics、Cheol K. Chung、Heather C. Johnson、Zhuqing Liu、Feng Peng、Stephan M. Rummelt、Zhiguo Jake Song、Lushi Tan、Lu Wang、Feng Xu

  DOI：10.1021/acs.orglett.2c03367

  日期：2022.10.21

  Herein, we present a strategy for the preparation of 3′-fluorinated nucleoside analogues via the aminocatalytic, electrophilic fluorination of readily accessible and bench-stable 2′-ketonucleosides. Initially developed to facilitate the manufacture of 3′-fluoroguanosine (3′-FG)─a substructure of anticancer therapeutic MK-1454─this strategy has been extended to the synthesis of a variety of 3′-fluoronucleosides

  在此，我们提出了一种通过易于获得且实验室稳定的 2'-酮核苷的氨基催化、亲电子氟化来制备 3'-氟化核苷类似物的策略。该策略最初是为了促进 3'-氟鸟苷 (3'-FG)（抗癌治疗药物 MK-1454 的一种子结构）的制造而开发的，现已扩展到多种 3'-氟核苷的合成。最后，我们展示了 2'-酮核苷合成子作为进一步多样化平台的实用性，并建议该方法应广泛适用于新型核苷类似物的发现。
• Selenoxide elimination for the synthesis of unsaturated-sugar uracil nucleosides
  作者：Kazuhiro Haraguchi、Hiromichi Tanaka、Hideaki Maeda、Yoshiharu Itoh、Shigeru Saito、Tadashi Miyasaka

  DOI：10.1021/jo00018a038

  日期：1991.8

  Introduction of a phenylseleno group to the sugar portion of uracil nucleosides and selenoxide elimination reactions of the resulting selenium-containing derivatives are described. A phenylselenide anion prepared by reducing (PhSe)2 with LialH4 was found to be highly reactive. By using this selenide as a nucleophile, ring openings of various types of cyclonucleosides and nucleosides having an anhydro structure in the sugar portion were accomplished. The products, which contain a phenylseleno group in the sugar portion, were oxidized with m-CPBA in CH2Cl2, and their susceptibility to the selenoxide elimination and regiochemistry of the reaction was investigated.
• Nucleosidic enol esters: A versatile tool for the synthesis of 3′-carbon-substituted nucleosides
  作者：Kazuhiro Haraguchi、Hiromichi Tanaka、Yoshiharu Itoh、Tadashi Miyasaka

  DOI：10.1016/s0040-4039(00)74884-2

  日期：1991.2

  Enol esters of uracil and adenine nucleosides prepared by selenoxide fragmentation of the corresponding 3'-phenylseleno derivatives have been shown to yield 3'-carbon-substituted products upon reacting with MeLi followed by electrophiles, providing the first example of the aldol reaction in this field.
• Synthesis of 2′-C-cyano-2′-deoxy- and 2′-C-cyano-2′,3′-dideoxy-β-d-arabinofuranosyl nucleosides
  作者：Sonsoles Velázquez、María-José Camarasa*

  DOI：10.1016/s0040-4020(01)88727-5

  日期：1992.2

  A series of 2'-C-cyano-2'-deoxy- and 2'-C-cyano-2',3'-dideoxy arabinofuranosyl nucleosides have been prepared by reaction of the corresponding 2'-ulosyl- and 3'-deoxy-2'-ulosyl nucleosides with sodium cyanide followed by 2'-deoxygenation of the cyanohyrins formed and removal of the protecting groups of the sugar moiety.