9-(3,5-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-2-ulosyl)adenine | 90813-59-5

• 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: 9-(3,5-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-2-ulosyl)adenine
• 英文别名: 9-(3,5-bis-O-TBDMS-β-D-erythro-pentofuran-2-ulosyl)adenine；(2R,4R,5R)-2-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-3-one
• CAS: 90813-59-5
• 化学式: C₂₂H₃₉N₅O₄Si₂
• 分子量: 493.754
• InChiKey: FVANHZXNITZCMB-WIBUTAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-(3,5-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-2-ulosyl)adenine 在 四丁基氟化铵 、 sodium tert-pentoxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 55.0h， 生成 9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-3-methylene-tetrahydro-furan-2-yl)-9H-purin-6-ol
  参考文献：
  名称：

  Nucleic acid related compounds. 70. Synthesis of 2'(and 3')-deoxy-2'(and 3')-methyleneadenosines and bis(methylene)furan 4',5'-didehydro-5'-deoxy-2'(and 3')-methyleneadenosines. Inhibitors of S-adenosyl-L-homocysteine hydrolase and ribonucleotide reductase

  摘要：

  Wittig treatment of 3',5'(or 2',5')-bis-O-silyl-2'(or 3')-ketoadenosine derivatives with methylenetriphenylphosphorane and deprotection gave the 2'(or 3')-deoxy-2'(or 3')-methyleneadenosines, respectively. Enzymatic deamination afforded the 2'(or 3')-deoxy-2'(or 3')-methyleneinosines. Treatment of 2'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-methylene-5'-O-tosyladenosine (14) with sodium 2-methyl-2-butoxide and deprotection gave 9-(3,5-dideoxy-3-methylene-beta-D-glycero-pent-4-enofuranosyl)adenine (20). Analogous treatment of a protected 2',5'-dideoxy-5'-iodo-2'-methyleneadenosine derivative gave 9-(2,5-dideoxy-2-methylene-beta-D-glycero-pent-4-enofuranosyl)adenine (22). Biochemical aspects of the putative mechanism-based inhibition of S-adenosyl-L-homocysteine hydrolase and ribonucleotide reductase by these compounds are discussed.

  DOI：

  10.1021/jo00025a029
• 作为产物：
  描述：

  腺苷 在 吡啶 、 chromium(VI) oxide 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 9-(3,5-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-2-ulosyl)adenine
  参考文献：
  名称：

  Nucleic acid related compounds. 70. Synthesis of 2'(and 3')-deoxy-2'(and 3')-methyleneadenosines and bis(methylene)furan 4',5'-didehydro-5'-deoxy-2'(and 3')-methyleneadenosines. Inhibitors of S-adenosyl-L-homocysteine hydrolase and ribonucleotide reductase

  摘要：

  Wittig treatment of 3',5'(or 2',5')-bis-O-silyl-2'(or 3')-ketoadenosine derivatives with methylenetriphenylphosphorane and deprotection gave the 2'(or 3')-deoxy-2'(or 3')-methyleneadenosines, respectively. Enzymatic deamination afforded the 2'(or 3')-deoxy-2'(or 3')-methyleneinosines. Treatment of 2'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-methylene-5'-O-tosyladenosine (14) with sodium 2-methyl-2-butoxide and deprotection gave 9-(3,5-dideoxy-3-methylene-beta-D-glycero-pent-4-enofuranosyl)adenine (20). Analogous treatment of a protected 2',5'-dideoxy-5'-iodo-2'-methyleneadenosine derivative gave 9-(2,5-dideoxy-2-methylene-beta-D-glycero-pent-4-enofuranosyl)adenine (22). Biochemical aspects of the putative mechanism-based inhibition of S-adenosyl-L-homocysteine hydrolase and ribonucleotide reductase by these compounds are discussed.

  DOI：

  10.1021/jo00025a029

文献信息

• Spiro-sulfamidate and sulfate nucleosides via 2′ and 3′-C-branched-chain sugars and nucleosides
  作者：Jérôme Lalot、Tony Tite、Anne Wadouachi、Denis Postel、Albert Nguyen Van Nhien

  DOI：10.1016/j.tet.2011.06.030

  日期：2011.8

  C-branched-chain sugars and nucleosides were obtained by organocatalysis from ulose derivatives. After a reduction step, the corresponding 1,3-diol was derivatized into 3′-spiro-sulfamidates and unexpected sulfates by treatment with a Burgess reagent. Deprotection of the Boc-derivatives was carried out while preserving the cyclic sulfate. An example of ring opening of the cyclic sulfate derivative

  通过有机催化从果糖衍生物获得C-支链糖和核苷。在还原步骤之后，通过用Burgess试剂处理，将相应的1，3-二醇衍生为3'-螺氨基磺酸盐和意外的硫酸盐。在保留环状硫酸盐的同时，进行Boc衍生物的脱保护。给出了环状硫酸盐衍生物与叠氮化钠开环导致相应的3'- C-叠氮烷基支链核苷的开环的实例。
• 2' And 3'-ketonucleosides and their arabino and xylo reduction products
  作者：Fritz Hansske、Danuta Madej、Morris J. Robins

  DOI：10.1016/0040-4020(84)85111-x

  日期：1984.1

  A number of 2',5'- or 3',5'-diprotected ribonucleosides and 5'-protected 2'- or 3'-deoxy-β-D-erythro-pentofuranosyl nucleosides have been oxidized to the corresponding 3' or 2'-ketonucleoside derivatives using chromium trioxide/pyridine/acetic anhydride or dimethyl sulfoxide/ acetic anhydride. Reduction of the carbonyl functions with sodium borohydride gave the inverted arabino, xylo, or deoxy-threo

  许多2'，5'-或3'，5'-双保护核糖核苷和5'-保护的2'-或3'-脱氧-β-D-赤型-戊呋喃糖基核苷已被氧化为相应的3'或2使用三氧化铬/吡啶/乙酸酐或二甲基亚砜/乙酸酐的'-酮核苷衍生物。用硼氢化钠还原羰基官能团，可以通过在糖环的受阻较少的α面上进行攻击，使倒位的阿拉伯糖，木糖或脱氧苏糖异构体成为主要产物。通过证明已经发生了原始羟基的完全氧化，使用硼氢化氘化钠的平行还原证实了差向异构体比率。氘标记还有助于进行NMR 频谱分配。
• A convenient synthesis of branched-chain nucleoside isothiocyanates <i>via</i> aza-Claisen rearrangement
  作者：Monika Tvrdoňová、Ján Elečko、Jozef Gonda

  DOI：10.1080/15257770.2021.1966799

  日期：2021.10.3

  introduction of a nitrogen atom at either C-2′ or C-3′ positions of nucleosides derived from uridine, 4-N-benzoylcytidine and adenosine was investigated. An efficient and rapid procedure was employed for creating new chiral centers at C-2′ and C-3′ positions using [3 De Clercq, E. Milestones in the Discovery of Antiviral Agents: Nucleosides and Nucleotides. Acta Pharm. Sin. B 2012, 2, 535–548. DOI: https://doi

  摘要 研究了在衍生自尿苷、4- N-苯甲酰胞苷和腺苷的核苷的 C-2' 或 C-3' 位置处立体控制地引入氮原子。采用高效快速的程序在 C-2' 和 C-3' 位置创建新的手性中心 [ 3 De Clercq, E. 抗病毒药物发现的里程碑：核苷和核苷酸。医药学报。罪。乙 2012年，2，535 - 548。_ DOI：https://doi.org/10.1016/j.apsb.2012.10.001。[交叉引用] ，[谷歌学术] ，3 De Clercq, E. 抗病毒药物发现的里程碑：核苷和核苷酸。医药学报。罪。乙 2012年，2，535 - 548。_ DOI：https://doi.org/10.1016/j.apsb.2012.10.001。[Crossref] , [Google Scholar]  ]-sigmatropic aza-Claisen 重排硫氰酸烯丙酯在常规和微波条件下。异硫氰酸酯产物的结构通过
• Nucleic acid related compounds. 60. Mild periodinane oxidation of protected nucleosides to give 2'- and 3'-ketonucleosides. The first isolation of a purine 2'-deoxy-3'-ketonucleoside derivative
  作者：Vicente Samano、Morris J. Robins

  DOI：10.1021/jo00305a003

  日期：1990.8
• SAMANO, VICENTE;ROBINS, MORRIS J., J. ORG. CHEM., 55,(1990) N8, C. 5186-5188
  作者：SAMANO, VICENTE、ROBINS, MORRIS J.

  DOI：——

  日期：——