9-<(1R,2S,3R)-4-t-butyldimethylsiloxymethyl-2,3-isopropylidenedioxycyclopentan-1-yl>adenine | 151266-98-7

• 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-<(1R,2S,3R)-4-t-butyldimethylsiloxymethyl-2,3-isopropylidenedioxycyclopentan-1-yl>adenine
• 英文别名: 5′-O-tert-butyldimethylsilyl-2′,3′-O-(isopropylidene)aristeromycin；9-((1R,2S,3R)-4-t-butyldimethylsiloxymethyl-2,3-isopropylidenedioxycyclopentan-1-yl)adenine；9-[(3aS,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]purin-6-amine
• CAS: 151266-98-7
• 化学式: C₂₀H₃₃N₅O₃Si
• 分子量: 419.599
• InChiKey: YIBHUUUOMIGUBU-XOUADPBQSA-N

物化性质

• 沸点：
  552.3±60.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  97.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-<(1R,2S,3R)-4-t-butyldimethylsiloxymethyl-2,3-isopropylidenedioxycyclopentan-1-yl>adenine 在 potassium tert-butylate 、 四丁基氟化铵 、 碘 、 N,N-二异丙基乙胺 、 potassium iodide 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 44.0h， 生成 (1S,2R,3R,5R)-3-(methoxymethyl)-5-[6-[[(3S)-1-[5-(trifluoromethyl)pyridin-2-yl]pyrrolidin-3-yl]amino]purin-9-yl]cyclopentane-1,2-diol
  参考文献：
  名称：

  The sequel to a carbocyclic nucleoside synthesis: a divergent access to both arenediazonium ions and aryl triflates

  摘要：

  Depending on the amount of acid used, treating aryl-dialkyl triazenes of general structure 3 with triflic acid resulted in the formation of either the corresponding arenediazonium triflates 4 or aryl triflates 8 apparently by two different pathways, the latter conversion being favoured at high acid concentration. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.147
• 作为产物：
  描述：

  (3aR,4S,6R,6aS)-2,2-Dimethyl-tetrahydro-cyclopenta[1,3]dioxole-4,6-dicarbaldehyde 在 吡啶 、 咪唑 、 sodium tetrahydroborate 、 phosphate buffer 、 18-冠醚-6 、 碘 、 sodium hydride 、 potassium carbonate 、 臭氧 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 16.0h， 生成 9-<(1R,2S,3R)-4-t-butyldimethylsiloxymethyl-2,3-isopropylidenedioxycyclopentan-1-yl>adenine
  参考文献：
  名称：

  实用的酶法合成（–）-阿霉素

  摘要：

  荧光假单胞菌脂肪酶（PFL）催化的内消旋化合物的不对称水解或酯交换反应已被用于（-）-阿霉素的合成1。

  DOI：

  10.1039/c39920001454

文献信息

• Highly asymmetric enzymatic hydrolysis and transesterification of meso-biscacetoxymethyl)- and bis(hydroxymethyl)cyclopentane derivatives: an insight into the active site model of Rhizopus Delemar lipase
  作者：Masakazu Tanaka、Miki Yoshioka、Kiyoshi Sakai

  DOI：10.1016/s0957-4166(00)80143-3

  日期：1993.5

  % ee. In explanation of these high enantioselectivities of RDL, the simple box-type active site model of enzyme was tentatively proposed. On the other hand, PFL-catalysed transesterification of meso-bis-(hydroxymethyl) cyclopentane (6) afforded (+)-16 of >99 % ee. The obtained (+) and (−)-16 were converted into the natural carbocyclic nucleoside (−)-aristeromycin (25), respectively.

  德氏根霉的脂肪酶（RDL）的水解-催化的内消旋-1,3-二（乙酰氧基甲基）环戊烷衍生物（7，12）和荧光假单胞菌脂肪酶（PFL）的水解-催化7个，得到手性单乙酸酯（15，16）的> 99％ee。为了解释RDL的高对映选择性，尝试性地提出了简单的盒型酶活性位点模型。另一方面，PFL催化的内消旋-双-（羟甲基）环戊烷（6）酯交换反应得到的（+）- 16 ee> 99％。将获得的（+）和（-）- 16转化为天然碳环核苷（-）-阿霉素（25）。
• Targeting <i>Mycobacterium tuberculosis</i> Biotin Protein Ligase (MtBPL) with Nucleoside-Based Bisubstrate Adenylation Inhibitors
  作者：Matthew R. Bockman、Alvin S. Kalinda、Riccardo Petrelli、Teresa De la Mora-Rey、Divya Tiwari、Feng Liu、Surendra Dawadi、Madhumitha Nandakumar、Kyu Y. Rhee、Dirk Schnappinger、Barry C. Finzel、Courtney C. Aldrich

  DOI：10.1021/acs.jmedchem.5b00719

  日期：2015.9.24

  Mycobacterium tuberculosis (Mtb), responsible for second leading cause of mortality among infectious diseases worldwide. Mycobacterial biotin protein ligase (MtBPL) is an both latent and symptomatic tuberculosis (TB), remains the essential enzyme in Mtb and regulates lipid metabolism through the post-translational biotinylation of acyl coenzyme A carboxylases. We report the synthesis and evaluation of a systematic series of potent nucleoside-based inhibitors of MtBPL that contain modifications to the ribofuranosyl ring of the nucleoside. All compounds were characterized by isothermal titration calorimetry (ITC) and shown to bind potently with K(D)s <= 2 nM. Additionally, we obtained high-resolution cocrystal structures for a majority of the compounds. Despite fairly uniform biochemical potency, the whole-cell Mtb activity varied greatly with minimum inhibitory concentrations (MIC) ranging from 0.78 to >100 mu M. Cellular accumulation studies showed a nearly 10-fold enhancement in accumulation of a C-2'-alpha analogue over the corresponding C-2'-beta analogue, consistent with their differential whole-cell activity.
• 8-Methyl Derivatives of Aristeromycin, Neplanocin, 3-Deazaneplanocin and Related Analogs
  作者：Stewart W. Schneller、Xueqiang Yin、Qi Chen、Wei Ye、Chong Li

  DOI：10.3987/com-16-s(s)36

  日期：——

  The promising biological properties of 8-methyladenosine prompted a study of the related carbocyclic analogs based on aristeromycin and neplanocin. These target compounds have been prepared from strategically protected parent carbocyclic nucleoside derivatives or built up from suitable cyclopentanols and cyclopentenols. Several of these nucleosides were evaluated against a variety of RNA and DNA viruses to determine the potential of the 8-methyl series as a source for new antiviral agents. Encouraging results towards Epstein-Barr virus, cowpox, vaccinia virus, Ebola, and the flaviviruses (dengue and yellow fever) suggests more extensive studies.