3',5'-Di-O-acetyl-uridin | 6773-48-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3',5'-Di-O-acetyl-uridin
• 英文别名: 3',5'-di-O-acetyluridine；3',5'-di-O-acetyl-uridine；[(2R,3S,4R,5R)-3-acetyloxy-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-2-yl]methyl acetate
• CAS: 6773-48-4
• 化学式: C₁₃H₁₆N₂O₈
• 分子量: 328.279
• InChiKey: PICUADGBUPLIHQ-HJQYOEGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3',5'-Di-O-acetyl-uridin 在 氨 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 2'-O-tert-butyloxycarbonyl-uridine
  参考文献：
  名称：

  A Convenient Pathway to 2?-(tert-Butyloxycarbonyl)ribonucleosides

  摘要：

  DOI：

  10.1002/prac.19923340616
• 作为产物：
  描述：

  2',3',5'-三乙酰尿苷 在 吡啶 、 氨 作用下， 生成 3',5'-Di-O-acetyl-uridin
  参考文献：
  名称：

  Brown et al., Journal of the Chemical Society, 1956, p. 2388,2392

  摘要：

  DOI：

文献信息

• An acetal group suitable for the protection of 2′-hydroxy functions in rapid oligoribonucleotide synthesis
  作者：Colin B Reese、Halina T Serafinowska、Giovanni Zappia

  DOI：10.1016/s0040-4039(00)84511-6

  日期：——

  as in ()] has an acid lability similar to that of the 4-methoxytetrahydropyran-4-yl (Mthp) protecting group under mild hydrolytic conditions [pH 2–3]; however, under the relatively more drastic conditions required for the complete removal of a 9-phenylxanthen-9-yl (Px) group, the Ctmp protecting group remains virtually intact.

  1-[（2-氯-4-甲基）苯基] -4-甲氧基哌啶-4-基[Ctmp，如（）]具有与4-甲氧基四氢吡喃-4-基（Mthp）相似的酸稳定性。温和水解条件[pH 2-3]下的保护基；但是，在完全除去9-苯基黄嘌呤-9-基（Px）基团所需的相对较苛刻的条件下，Ctmp保护基团实际上保持完整。
• Regioselective enzymatic acylation of pharmacologically interesting nucleosides in 2-methyltetrahydrofuran, a greener substitute for THF
  作者：Yolanda Simeó、José Vicente Sinisterra、Andrés R. Alcántara

  DOI：10.1039/b818992g

  日期：——

  1-β-Arabinofuranosyl uracil, 9-β-arabinofuranosyl adenosine, 2′-O-(2-methoxyethyl)-5-methyl uridine, adenosine and uridine were enzymatically acylated with hexanoic anhydride and vinyl esters by CALB lipase (lipase B from Candida antarctica) with excellent regioselectivity in many cases and analytical reaction yields above 90%. The influence of the stereochemistry of the hydroxyl group on C-2′ was studied. Some of these esterifications were carried out in 2-methyltetrahydrofuran (MeTHF), which is described as an excellent substitute for THF in biocatalysed processes in organic media. This application for this green solvent is a proof-of-concept opening the use of MeTHF in biotransformations.

  1-β-阿拉伯呋喃糖基尿嘧啶、9-β-阿拉伯呋喃糖基腺苷、2′-O-(2-甲氧基乙基)-5-甲基尿苷、腺苷和尿苷在南极假丝酵母酯酶B（CALB）的催化下，与己酸酐和乙烯酯进行酶法酰化反应，具有优异的区域选择性，反应产率高于90%。研究了C-2′羟基的立体化学性质对反应的影响。一些酰化反应在2-甲基四氢呋喃（MeTHF）中进行，该溶剂被认为是生物催化过程中有机介质中四氢呋喃的优良替代品。这种绿色溶剂的应用验证了其在生物转化中使用的概念，为MeTHF的应用开辟了道路。
• An improved procedure for the acetalisation of alcoholic hydroxyl functions
  作者：H. C. P. F. Roelen、G. J. Ligtvoet、G. A. van der Marel、J. H. van Boom

  DOI：10.1002/recl.19871061008

  日期：——

  Acetalisation of 3′,5′-di-O-acetyluridine in DMF with 4,4-dimethoxytetrahydro-4H-pyran and 4,4-dimethoxytetrahydro-4H-1-thiopyran in the presence of trimethylsilyl chloride (TMSiCl) afforded, after removal of the acetyl groups, 2′-O-(4-methoxytetrahydropyranyl)-uridine and its sulfur analogue, respectively. It was also established that a 3′,5′-O-(tetraisopropyldisiloxane-1,3-diyl) protected ribonucleoside

  去除后，在存在三甲基甲硅烷基氯（TMSiCl）的情况下，将3'，5'-二-O-乙酰尿苷在DMF中与4,4-二甲氧基四氢-4H-吡喃和4,4-二甲氧基四氢-4H-1-硫吡喃缩醛化。的乙酰基分别为2′-O-（4-甲氧基四氢吡喃基）-尿苷及其硫类似物。还确定了使用TMSiCl促进的缩醛化方法将3'，5'-O-（四异丙基二硅氧烷-1,3-二基）保护的核糖核苷快速异构化为相应的2'，3'-异构体。
• 2′-(trimethylsilyl)ethoxymethyl protection of the 2′-hydroxyl group in oligoribonucleotide synthesis
  作者：Francine E. Wincott、Nassim Usman

  DOI：10.1016/0040-4039(94)85015-1

  日期：1994.9

  2′-O-[(Trimethylsilyl)ethoxymethyl]-5′-O-dimethoxytrityl uridine 3′-(2-cyanoethyl-N,N-diisopropylphosphoramidite) (1) was synthesized from dimethoxytrityl uridine (2) in two steps. The amidite was then incorporated into a (Up)9U polymer. Removal of the (trimethylsilyl)ethoxymethyl (SEM) group was effected with BF3•OEt2 in 30 min.

  2′- O -[（三甲基甲硅烷基）乙氧基甲基] -5′- O-二甲氧基三苯甲基尿苷3′-（2-氰基乙基-N，N-二异丙基亚氨基膦酸酯）（1）由二甲氧基三苯甲基尿苷（2）合成。然后，将亚酰胺被纳入一个（上）9 U聚合物。在30分钟内用BF 3 •OEt 2去除（三甲基甲硅烷基）乙氧基甲基（SEM）基团。
• Ishido, Yoshiharu; Sakairi, Nobuo; Okazaki, Kei, Journal of the Chemical Society. Perkin transactions I, 1980, p. 563 - 573
  作者：Ishido, Yoshiharu、Sakairi, Nobuo、Okazaki, Kei、Nakazaki, Nobuo

  DOI：——

  日期：——