1-methoxy-2,3-O-isopropylidene-L-ribofuranose | 263708-32-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methoxy-2,3-O-isopropylidene-L-ribofuranose
• 英文别名: [(3aR,4R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methanol；[(3aS,6S,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol
• CAS: 263708-32-3
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: DXBHDBLZPXQALN-FKMOCYPUSA-N

物化性质

• 沸点：
  287.3±40.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-methoxy-2,3-O-isopropylidene-L-ribofuranose 在 10percent Pd/C 氢氧化钾 、 氢气 、 溴 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 1-methoxy-2,3-O-isopropylidene-5-deoxy-L-ribofuranose
  参考文献：
  名称：

  Monocyclic l-Nucleosides with Type 1 Cytokine-Inducing Activity

  摘要：

  A series of 1,2,4-triazole L-nucleosides were synthesized and evaluated for their ability to stimulate type 1 cytokine production by activated human T cells in direct comparison to the known active agent ribavirin. Among the compounds prepared, 1-beta-L-ribofuranosyl-1,2,4-triazole-3-carboxamide (5, ICN 17261) was found to be the most uniformly potent compound. Conversion of the 3-carboxamide group of 5 to a carboxamidine functionality resulted in 1-beta-ribofuranosyl-1,2,4-triazole-3-carboxamidine hydrochloride(10), which induced cytokine levels comparable to 5 for two of the three type 1 cytokines examined. Modification of the carbohydrate moiety of 5 provided compounds of reduced activity. Significantly, ICN 17261 offers interesting immunomodulatory potential for the treatment of diseases where type 1 cytokines play an important role.

  DOI：

  10.1021/jm9905514
• 作为产物：
  描述：

  甲醇 、 L-呋喃核糖 、 丙酮 生成 1-methoxy-2,3-O-isopropylidene-L-ribofuranose
  参考文献：
  名称：

  Structure−Activity Relationship of (N)-Methanocarba Phosphonate Analogues of 5′-AMP as Cardioprotective Agents Acting Through a Cardiac P2X Receptor

  摘要：

  P2X receptor activation protects in heart failure models. MRS2339 3, a 2-chloro-AMP derivative containing a (N)-methanocarba (bicyclo[3.1.0]hexane) system, activates this cardioprotective channel. Michaelis-Arbuzov and Wittig reactions provided phosphonate analogues of 3, expected to be stable in vivo due to the C P bond. After chronic administration via a mini-osmotic pump (Alzet), some analogues significantly increased intact heart contractile function in calsequestrin-overexpressing mice (genetic model of heart failure) compared to vehicle-infused mice (all inactive at the vasodilatory P2Y(1) receptor). Two phosphonates, (1'S,2'R,3',5,4'R,5'S)-4'-(6-amino-2-chloropurin-9-y1)-2',3'-(dihydroxy)-1'-(phosphonomethylene)-bicyclo[3.1.0]hexane, 4 (MRS2775), and its homologue 9 (MRS2935), both 5'-saturated, containing a 2-Cl substitution, improved echocardiography-derived fractional shortening (20.25% and 19.26%, respectively, versus 13.78% in controls), while unsaturated 5'-extended phosphonates, all 2-H analogues, and a CH3-phosphonate were inactive. Thus, chronic administration of nucleotidase-resistant phosphonates conferred a beneficial effect, likely via cardiac P2X receptor activation. Thus, we have greatly expanded the range of carbocyclic nucleotide analogues that represent potential candidates for the treatment of heart failure.

  DOI：

  10.1021/jm9018542

文献信息

• Synthesis of Biologically Active Piperidine Metabolites of Clopidogrel: Determination of Structure and Analyte Development
  作者：Scott A. Shaw、Balu Balasubramanian、Samuel Bonacorsi、Janet Caceres Cortes、Kevin Cao、Bang-Chi Chen、Jun Dai、Carl Decicco、Animesh Goswami、Zhiwei Guo、Ronald Hanson、W. Griffith Humphreys、Patrick Y. S. Lam、Wenying Li、Arvind Mathur、Brad D. Maxwell、Quentin Michaudel、Li Peng、Andrew Pudzianowski、Feng Qiu、Shun Su、Dawn Sun、Adrienne A. Tymiak、Benjamin P. Vokits、Bei Wang、Ruth Wexler、Dauh-Rurng Wu、Yingru Zhang、Rulin Zhao、Phil S. Baran

  DOI：10.1021/acs.joc.5b00632

  日期：2015.7.17

  Clopidogrel is a prodrug anticoagulant with active metabolites that irreversibly inhibit the platelet surface GPCR P2Y12 and thus inhibit platelet activation. However, gaining an understanding of patient response has been limited due to imprecise understanding of metabolite activity and stereochemistry, and a lack of acceptable analytes for quantifying in vivo metabolite formation. Methods for the

  氯吡格雷是具有活性代谢产物的前药抗凝剂，其不可逆地抑制血小板表面GPCR P2Y 12并因此抑制血小板活化。然而，由于对代谢物活性和立体化学的不精确了解，以及缺乏用于量化体内代谢物形成的可接受分析物，对患者反应的了解受到了限制。公开了用于产生氯吡格雷的所有生物活性代谢物，其立体化学分配以及通过三种概念上正交的途径开发稳定的分析物的方法。
• Spontaneous Symmetry Breaking in the Formation of Supramolecular Polymers: Implications for the Origin of Biological Homochirality
  作者：Suneesh C. Karunakaran、Brian J. Cafferty、Angela Weigert‐Muñoz、Gary B. Schuster、Nicholas V. Hud

  DOI：10.1002/anie.201812808

  日期：2019.1.28

  macroscopic homochiral domains of supramolecular polymers. These assemblies exhibit a high degree of chiral amplification. Addition of a small quantity of one handedness of a chiral derivative of CyCo6 generates exclusively homochiral structures. This system exhibits the highest reported degree of chiral amplification for dynamic helical polymers or supramolecular helices. Significantly, homochiral

  非手性，单体，核碱基模拟物（2,4,6-三氨基嘧啶，TAP和氰尿酸衍生物，CyCo6）的水溶液自发组装成超分子聚合物的宏观同手性结构域。这些组装物表现出高度的手性扩增。CyCo6的少量单手性手性衍生物的添加仅产生同手性结构。对于动态螺旋聚合物或超分子螺旋，该系统显示出最高的手性扩增程度。重要的是，由氰尿酸（Cy）和核糖核苷酸（l-，d‐pTARC）是TAP与糖类反应自发产生的。这些发现支持以下假设：核酸同手性是超分子聚合物水平上对称性破坏的结果。