2-amino-3',5'-bis(O-t-butyldimethylsilyl)-β-D-arabinofurano<1',2':4,5>-2-oxazoline | 64332-51-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-3',5'-bis(O-t-butyldimethylsilyl)-β-D-arabinofurano<1',2':4,5>-2-oxazoline
• 英文别名: 2-amino-3',5'-bis(O-t-butyldimethylsilyl)-β-D-arabinofurano[1',2':4,5]-2-oxazoline；(3aR,5R,6R,6aS)-6-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]oxazol-2-amine
• CAS: 64332-51-0
• 化学式: C₁₈H₃₈N₂O₄Si₂
• 分子量: 402.682
• InChiKey: CVEHDJJFCYEDGA-APIJFGDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-3',5'-bis(O-t-butyldimethylsilyl)-β-D-arabinofurano<1',2':4,5>-2-oxazoline 在 吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 36.0h， 生成 3-N-acetyl-2-ureido-3',5'-bis(O-t-butyldimethylsilyl)-β-D-arabinofurano<1',2':4,5>oxazoline
  参考文献：
  名称：

  某些6-烷硫基-2,2'-脱水-5-氮杂尿苷的合成†

  摘要：

  β-d阿糖呋喃并[1'，2'：4,5] oxazolo-小号三嗪-4-酮-6-硫酮（7B）及其吨丁基二保护的对应图7a是通过处理相应的2-氨基-合成β-D-阿拉伯呋喃酮[1'，2'：4,5] -2-恶唑啉与乙氧羰基异硫氰酸酯。这些2,2'-脱水-小号然后嗪核苷类似的反应条件下进行烷基化。的3烷基化'，5'-双（OT丁基二）-β-d阿糖呋喃并[1'，2'： - 4,5] oxazolo-小号三嗪-4-酮-6-硫酮（7A）中提供的靶向的S-烷基化核苷，即C6-SCH 3（9a），C6-SCH 2 -CH = CH 2（10a）和C6-S-CH 2 -C = CH（11a），产率合理。尝试将这些核苷脱保护失败。为了避免该问题，用相同的试剂将7b烷基化。在每种情况下的，而不是预期的S-烷基化的脱水核苷，5-的混合物Ñ -alkylanhydro-小号和5-三嗪-4,6-二酮Ñ -alkylanhy

  DOI：

  10.1002/jhet.5570270350
• 作为产物：
  描述：

  阿拉伯糖 在 咪唑 、 potassium hydrogencarbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 2-amino-3',5'-bis(O-t-butyldimethylsilyl)-β-D-arabinofurano<1',2':4,5>-2-oxazoline
  参考文献：
  名称：

  [EN] OLIGONUCLEOTIDE COMPOSITIONS AND METHODS THEREOF
  [FR] COMPOSITIONS D'OLIGONUCLÉOTIDES ET PROCÉDÉS ASSOCIÉS

  摘要：

  除其他事项外，本公开提供寡核苷酸及其组合物。在某些实施例中，提供的寡核苷酸及其组合物对腺苷修饰有用。在某些实施例中，本公开提供了治疗各种需要腺苷修饰的疾病、疾病或病症的方法。

  公开号：

  WO2022099159A1

文献信息

• Diastereomeric 5,6-Dihydrothymidines. Preparation, Stereochemical Assignments, and MnO2 Oxidation Studies of Thymidines
  作者：Palle V. P. Pragnacharyulu、Chandra Vargeese、Michael Mc Gregor、Elie Abushanab

  DOI：10.1021/jo00115a026

  日期：1995.5

  A useful method for the stereospecific synthesis of beta-thymidine and beta-5,6-dihydrothymidine nucleosides is described. Condensation of methyl 2-formylpropionate and methyl methacrylate with oxazolines 8 furnished the corresponding 2,2'-anhydrothymidine 11 and a 2:1 diastereomeric mixture of 2,2'-anhydro-5,6-dihydrothymidine 10, respectively. While DDQ oxidation of 10 furnished 11, active MnO2 resulted in a selective dehydrogenation hitherto unreported in nucleoside chemistry. The minor diasteromer 10b was quantitatively converted to 11, leaving 10a unchanged. A plausible explanation for this selectivity was based on the stereochemistry at C5 which was determined by one-dimensional NOE studies.
• .beta.-D-Arabinofuran[1',2':4,5]oxazolo-1,3,5-triazine-5-N-methyl-4,6-dione and analogs, unusually specific immunosuppressive agents
  作者：W. Wierenga、B. E. Loughman、A. J. Gibbons、H. E. Renis

  DOI：10.1021/jm00204a011

  日期：1978.6

  Sequential treatment of the protected beta-D-arabinofuran[1',2':4,5]-2-aminooxazoline (2) with methyl isocyanate and diimidazole carbonyl afforded the 2,2'-anhydro-beta-D-arabinofuranosyl nucleoside, 6. Deprotection and hydrolysis yielded the corresponding arabinoside. Although the anhydronucleoside exhibited in vitro antiviral activity against herpes simplex type 1, it exacerbated the infection in vivo. Further examination uncovered an in vitro inhibition of the induction of a cell-mediated immune response without cytotoxicity.
• Introduction of a new 1,3-electrophilic carbon-nitrogen-carbon annulation reagent in the synthesis of 2,2'-anhydrodihydro-5-azathymidine
  作者：Wendell Wierenga、John A. Woltersom

  DOI：10.1021/jo00398a001

  日期：1978.2
• Schroeder, A. C.; Srikrishnan, T.; Parthasarathy, R., Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 571 - 574
  作者：Schroeder, A. C.、Srikrishnan, T.、Parthasarathy, R.、Bloch, A.

  DOI：——

  日期：——
• Synthesis and in vitro cytostatic activity of new β - d -arabino furan[1′,2′:4,5]oxazolo- and arabino-pyrimidinone derivatives
  作者：Jean-Jacques Bosc、Laurent Latxague、Jean-Michel Léger、Jan Balzarini、Isabelle Forfar、Christian Jarry、Jean Guillon

  DOI：10.1016/j.ejmech.2009.10.032

  日期：2010.2

  A series of nucleoside derivatives was obtained via heteroatom annulation of the amino oxazoline Of D(-)-arabinose. Unequivocal proofs for the stereostructure of some new arabinosyl pyrimidinone derivatives were obtained by X-ray structure analysis. These newly synthesized compounds were then evaluated for their cytostatic activity against murine leukemia (L1210), and human T-lymphocytes (Molt 4/C8 and CEM). Of all the compounds in the series, the protected silylated tricyclic fused pyrimidinone 10 showed the most significant antitumor activity against murine leukemia L1210 (IC50 = 6 mu M), and human T-lymphocytes cells Molt 4/C8 (IC50 = 7.9 mu M) and CEM/0 cell lines (IC50 = 7.5 mu M). None of the compounds exhibited significant antiviral inhibitory activities. (C) 2009 Elsevier Masson SAS. All rights reserved.