3,5-bis(toluoyl)-2-deoxyribosyl chloride | 52162-55-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-bis(toluoyl)-2-deoxyribosyl chloride
• 英文别名: 3,5-di-O-(P-toluyl)-2-deoxy-D-*ribofuranosyl chlo；(2R,3S)-5-chloro-3-(4-methylphenoxy)-2-[(4-methylphenoxy)methyl]oxolane
• CAS: 52162-55-7
• 化学式: C₁₉H₂₁ClO₃
• 分子量: 332.827
• InChiKey: VJQUMYQNPLTFOB-PAMZHZACSA-N

物化性质

• 沸点：
  467.3±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-bis(toluoyl)-2-deoxyribosyl chloride 在 镍 吡啶 、 2,2,2-三氟-N,N-二(三甲硅基)乙酰胺 、 氢气 、 四氯化锡 作用下， 以 甲醇 、 丙酮 为溶剂， -45.0~25.0 ℃ 、101.33 kPa 条件下， 反应 17.75h， 生成 (8R)-3-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepin-8-ol
  参考文献：
  名称：

  Total synthesis of (8R)-3-(2-deoxy-.beta.-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (pentostatin), the potent inhibitor of adenosine deaminase

  摘要：

  DOI：

  10.1021/jo00139a015

文献信息

• Nucleotides and nucleosides and methods for their use in DNA sequencing
  申请人：Lasergen, Inc.

  公开号：US09200319B2

  公开（公告）日：2015-12-01

  The present invention relates generally to labeled and unlabled cleavable terminating groups and methods for DNA sequencing and other types of DNA analysis. More particularly, the invention relates in part to nucleotides and nucleosides with chemically cleavable, photocleavable, enzymatically cleavable, or non-photocleavable groups and methods for their use in DNA sequencing and its application in biomedical research.

  本发明一般涉及带标记和未标记的可切割终止基团以及用于DNA测序和其他类型的DNA分析的方法。更具体地，该发明部分涉及具有化学可切割、光解可切割、酶可切割或非光解可切割基团的核苷酸和核苷以及它们在DNA测序中的使用方法及其在生物医学研究中的应用。
• [EN] INDOLIN-2-ONE OR PYRROLO-PYRIDIN/PYRIMIDIN-2-ONE DERIVATIVES<br/>[FR] DÉRIVÉS INDOLIN-2-ONE OU PYRROLO-PYRIDIN/PYRIMIDIN-2-ONE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014202493A1

  公开（公告）日：2014-12-24

  The present invention is concerned with 2-oxo-2,3-dihydro-indoles of general formula (I) wherein Ar is a heteroaryl group, containing one, two or three heteroatoms, selected from N, S or O; R1 is hydrogen, lower alkyl, halogen, amino, dimethylamino, cyano, lower alkyl substituted by halogen, lower alkyl substituted by hydroxy, CH(OH)CF3, (CH2)o-lower alkoxy, cycloalkyl optionally substituted by CF3, or heterocycloalkyl optionally substituted by lower alkyl; R2 is hydrogen, lower alkyl, (CH2)o-cycloalkyl, (CH2)o-O-cycloalkyl, (CH2)o-lower alkoxy, CH2)o-lower alkoxy substituted by halogen, (CH2)o-heterocycloalkyl optionally substituted by lower alkyl, (CH2)o-S(O)2-cycloalkyl, lower alkyl substituted by one or two hydroxy, lower alkyl substituted by one or two lower alkoxy, (CH2)o-S(O)2-lower alkyl, lower alkyl substituted by halogen or CH2CH(OH)CF3; R3 is halogen or lower alkyl; X is CH or N; X1 is CH or N; n is 1 or 2; o is 0, 1, 2 or 3; m is 0, 1 or 2; and the dotted line is a bond or not; as well as with a pharmaceutically acceptable salts thereof, with a racemic mixture, or with its corresponding enantiomer and/or optical isomer and/or stereoisomer thereof The compounds may be used for the treatment of certain central nervous system disorders which are positive (psychosis) and negative symptoms of schizophrenia, substance abuse, alcohol and drug addiction, obsessive-compulsive disorders, cognitive impairment, bipolar disorders, mood disorders, major depression, treatment resistant depression, anxiety disorders, Alzheimer's disease, autism, Parkinson's disease, chronic pain, borderline personality disorder, sleep disturbances, chronic fatigue syndrome, stiffness, antiinflammatory effects in arthritis and balance problems.

  本发明涉及通式（I）中的2-氧代-2,3-二氢吲哚，其中Ar是一个杂环烃基，含有一个、两个或三个杂原子，选自N、S或O；R1是氢、低碳基、卤素、氨基、二甲胺基、氰基、被卤素取代的低碳基、被羟基取代的低碳基、CH(OH)CF3、（CH2）o-低碳醚、环烷基（可选地被 取代）、或杂环烷基（可选地被低碳基取代）；R2是氢、低碳基、（ ）o-环烷基、（ ）o-O-环烷基、（ ）o-低碳醚、被卤素取代的（ ）o-低碳醚、（ ）o-杂环烷基（可选地被低碳基取代）、（ ）o-S(O)2-环烷基、被一个或两个羟基取代的低碳基、被一个或两个低碳醚取代的低碳基、（ ）o-S(O)2-低碳基、被卤素或 CH(OH) 取代的低碳基；R3是卤素或低碳基；X是CH或N；X1是CH或N；n是1或2；o是0、1、2或3；m是0、1或2；虚线是键或非键；以及其在药学上可接受的盐、消旋混合物、或其相应的对映体和/或光学异构体和/或立体异构体。这些化合物可用于治疗某些中枢神经系统障碍，包括精神病（阳性和阴性症状）、精神分裂症、物质滥用、酒精和药物成瘾、强迫症、认知障碍、双相情感障碍、情绪障碍、重性抑郁症、治疗难治性抑郁症、焦虑障碍、阿尔茨海默病、自闭症、帕金森病、慢性疼痛、边缘人格障碍、睡眠障碍、慢性疲劳综合征、僵硬、关节炎的抗炎作用和平衡问题。
• Nucleoside und Nucleotide Teil 27 Festphasensynthese eines Tridecanucleosid-dodecaphosphats, das die unnatürliche Base 4-Amino-2(1<i>H</i>)-pyridinon enthält, und eines Octanucleosid-heptaphosphats zur Untersuchung der DNA-Polymerase-Spezifität
  作者：Roland Charczuk、Christoph Tamm

  DOI：10.1002/hlca.19870700321

  日期：1987.5.6

  Nucleosides and Nucleotides. Solid Phase Synthesis of a Tridecanucleoside Dodecaphosphate Containing the Unnatural Base 4-Amino-2(1H)-pyridinone and of a Octanucleoside Heptaphosphate for the Determination of the DNA-Polymerase Specificity

  核苷和核苷酸。固相合成包含非天然碱4-氨基-2（1 H）-吡啶酮的十三碳核苷十二磷酸和八磷酸核苷七磷酸以确定DNA聚合酶的特异性
• Uracil derivatives. V. Syntheses and growth-inhibitory activity against L-1210 cells of 5-substituted 2'-deoxyuridines and orotidine derivatives.
  作者：JUTARO OKADA、KOICHI NAKANO、HIROSHI MIYAKE

  DOI：10.1248/cpb.33.856

  日期：——

  5-Benzyloxymethyl-2'-deoxyuridine 3', 5'-di-p-toluate (III), a key intermediate in the preparation of 5-substituted 2'-deoxyuridines (VIa-d), was prepared in satisfactory yield. 5-(4-Substituted phenylthiomethyl)-2'-deoxyuridines (VIa-d) were synthesized in three steps from III. The reaction of silylated orotates (VIIa-e) with 1-O-acetyl-2, 3, 5-tri-O-benzoyl-β-D-ribofuranose (VIII) gave the N1, N3-bisribosides (IXa-e) and the N3-ribosides (Xa-e). The N3-ribosides (Xa-e) were deprotected to give the N3-nucleosides (XIa-e). Compounds VIa-d and XIa-e were tested for ability to inhibit the growth of L-1210 cells in vitro.

  5-苄氧基甲基-2'-脱氧尿苷3', 5'-二对甲苯甲酸酯(III)是制备5-取代的2'-脱氧尿苷(VIa-d)的关键中间体，其收率令人满意。从III开始分三个步骤合成5-(4-取代的苯硫基甲基)-2'-脱氧尿苷(VIa-d)。甲硅烷基化乳清酸酯(VIIa-e)与1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-D-呋喃核糖(VIII)反应得到N1,N3-双核糖苷(IXa-e)和N3-核苷（Xa-e）。将N3-核苷(Xa-e)去保护以得到N3-核苷(XIa-e)。测试了化合物VIa-d和XIa-e在体外抑制L-1210细胞生长的能力。
• An efficient synthesis tetrazole and oxadiazole analogues of novel 2′-deoxy-C-nucleosides and their antitumor activity
  作者：Srishylam Penjarla、Subir Kumar Sabui、Dhande Sudhakar Reddy、Shyamapada Banerjee、Paidi Yella Reddy、Santhosh Penta、Yogesh S. Sanghvi

  DOI：10.1016/j.bmcl.2020.127612

  日期：2020.12

  Various tetrazole and oxadiazole C-nucleoside analogues were synthesized starting from pure α- or β-glycosyl-cyanide. The synthesis of glycosyl-cyanide as key precursor was optimized on gram-scale to furnish crystalline starting material for the assembly of C-nucleosides. Oxadizole C-nucleosides were synthesized via two independent routes. First, the glycosyl-cyanide was converted into an amidoxime

  从纯的α-或β-糖基氰化物开始合成了各种四唑和恶二唑C-核苷类似物。在克规模上优化了作为主要前体的糖基氰化物的合成，以提供用于C-核苷组装的结晶原料。草酸二唑C-核苷是通过两种独立的途径合成的。首先，将糖基氰化物转化为an胺肟，其在闭环时为有效地组装1,2,4-乙二唑提供了另一种途径。其次，将糖基氰化物的两个端基异构体都转化为四唑核苷，然后进行酰基化重排，从而以高收率提供了1,3,4-恶二唑。这些协议可轻松获得原本难以合成的C-核苷，并具有良好的收率和保护基团的兼容性。评价这些C-核苷的抗肿瘤活性。这项工作为便利用于药物发现的新化学实体库的组装铺平了道路。