5-O-(4-chlorobenzoyl)-1,2-O-isopropylidene-D-xylofuranose | 199787-14-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-O-(4-chlorobenzoyl)-1,2-O-isopropylidene-D-xylofuranose
• 英文别名: 5-O-(4-chlorobenzoyl)-1,2-O-isopropylidene-α-D-xylofuranose；[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl 4-chlorobenzoate
• CAS: 199787-14-9
• 化学式: C₁₅H₁₇ClO₆
• 分子量: 328.749
• InChiKey: WEMCTPNXVCRFAG-GFQSEFKGSA-N

物化性质

• 沸点：
  455.4±40.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-O-(4-chlorobenzoyl)-1,2-O-isopropylidene-D-xylofuranose 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 tri-chlorocyanuric acid 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以77%的产率得到5-O-(4-chlorobenzoyl)-1,2-O-isopropylidene-D-erythro-pentofuranose03-urose
  参考文献：
  名称：

  受保护的核苷3'-磷酸的膦硫代二氟亚甲基类似物的第二代合成

  摘要：

  描述了一种实用的八步合成关键中间体14的方法，该方法可从α-d-木糖获得19％的总收率。制备可以以克为单位进行，并且涉及有机镁试剂2d的使用。制备15可证明衍生物14转化为标题化合物的能力。此外，中间体12的X射线晶体学提供了有关二氟硫代磷酸酯的第一结构数据。

  DOI：

  10.1016/j.tet.2004.03.082
• 作为产物：
  描述：

  1,2:3,5-双-O-异亚丙基-alpha-D-呋喃木糖 在 ammonium cerium(IV) nitrate 、 TEA 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 18.0h， 生成 5-O-(4-chlorobenzoyl)-1,2-O-isopropylidene-D-xylofuranose
  参考文献：
  名称：

  受保护的核苷3'-磷酸的膦硫代二氟亚甲基类似物的第二代合成

  摘要：

  描述了一种实用的八步合成关键中间体14的方法，该方法可从α-d-木糖获得19％的总收率。制备可以以克为单位进行，并且涉及有机镁试剂2d的使用。制备15可证明衍生物14转化为标题化合物的能力。此外，中间体12的X射线晶体学提供了有关二氟硫代磷酸酯的第一结构数据。

  DOI：

  10.1016/j.tet.2004.03.082

文献信息

• D-pentofuranose derivatives and process for preparing the same
  申请人：Taiho Pharmaceutical Co., Ltd.

  公开号：US05880294A1

  公开（公告）日：1999-03-09

  The present invention relates to D-pentofuranose derivatives represented by the following formulas (1) through (4): ##STR1## (wherein A represents a chlorobenzoyl group; R.sup.1 represents a hydrogen atom, an aliphatic lower acyl group, a substituted or unsubstituted benzoyl group; each of X and Y represents a lower alkyl group; Z represents an ethynyl group or tri-lower alkyl silylethynyl group; the sugar moiety in formula (1) represents xylose; and the sugar moiety of each of formulas (3) and (4) represents ribose). The present invention also relates to a process for preparing the compound (2) characterized by oxidizing the compound of formula (1) with a hypochlorite in the presence of a catalytic amount of 2,2,6,6-tetramethylpiperidinoxy compound, and these compounds are useful as intermediates in the synthesis of 3'-C-substituted ribonucleoside derivatives having excellent antitumor activities.

  本发明涉及通式(1)至(4)所示的D-戊呋喃糖衍生物：##STR1##（其中A代表氯苯甲酰基；R1代表氢原子、低级脂肪族酰基、取代或未取代的苯甲酰基；X和Y各自代表低级烷基；Z代表乙炔基或三低级烷基硅乙炔基；式(1)中的糖部分代表木糖；式(3)和(4)中的糖部分各自代表核糖）。本发明还涉及制备化合物(2)的方法，其特征在于在2,2,6,6-四甲基哌啶氧基化合物催化量的存在下，用次氯酸盐氧化式(1)的化合物，这些化合物作为合成具有优异抗肿瘤活性的3'-C-取代的核糖核苷衍生物的中间体是有用的。
• Synthesis and anti-trypanosomal activity of 3′-fluororibonucleosides derived from 7-deazapurine nucleosides
  作者：Van Hai Nguyen、Michal Tichý、Samanta Rožánková、Radek Pohl、A. Michael Downey、Eva Doleželová、Eva Tloušťová、Martina Slapničková、Alena Zíková、Michal Hocek

  DOI：10.1016/j.bmcl.2021.127957

  日期：2021.5

  report the synthesis and biological profiling of 3′-deoxy-3′-fluororibonucleosides derived from 7-deazaadenine nucleosides bearing diverse substituents at position 7. They were synthesized through glycosylation of 6-chloro-7-bromo- or -7-iodo-7-deazapurine with protected 3′-fluororibose followed by cross-coupling reactions at position 7 and/or deprotection. Most of the title nucleosides displayed micromolar

  布氏锥虫寄生虫会导致人类非洲锥虫病，目前治疗该病的药物通常效率低下且有毒。这促使需要开发新的抗锥虫病药物。我们报告了 3'-deoxy-3'-fluororibonucleosides 的合成和生物学分析，该核苷衍生自 7-deazaadenine 核苷，在 7 位具有不同的取代基。它们是通过 6-chloro-7-bromo- 或 -7-iodo- 的糖基化合成的。 7-脱氮嘌呤与受保护的 3'-氟核糖，随后在 7 位发生交叉偶联反应和/或脱保护。大多数标题核苷显示出针对布氏锥虫的微摩尔或亚微摩尔活性。最活跃的是 7-溴和 7-碘衍生物，它们对T.B. 布鲁塞和T. b. gambiense并且没有细胞毒性，因此代表了进一步发展的有希望的候选者。
• D-PENTOFURANOSE DERIVATIVES AND PROCESS FOR THE PREPARATION THEREOF
  申请人：TAIHO PHARMACEUTICAL COMPANY, LIMITED

  公开号：EP0842942A1

  公开（公告）日：1998-05-20

  The present invention relates to D-pentofuranose derivatives represented by the following formulas (1) through (4): (wherein A represents a chlorobenzoyl group; R1 represents a hydrogen atom, an aliphatic lower acyl group, a substituted or unsubstituted benzoyl group; each of X and Y represents a lower alkyl group; Z represents an ethynyl group or tri-lower alkyl silylethynyl group; the sugar moiety in formula (1) represents xylose; and the sugar moiety of each of formulas (3) and (4) represents ribose). The present invention also relates to a process for preparing the compound (2) characterized by oxidizing the compound of formula (1) with a hypochlorite in the presence of a catalytic amount of 2,2,6,6-tetramethylpiperidinoxy compound. These compounds are useful as intermediates in the synthesis of 3'-C-substituted ribonucleoside derivatives having excellent antitumor activities.

  本发明涉及由下式(1)至(4)代表的D-戊呋喃糖衍生物： (其中A代表氯代苯甲酰基；R1代表氢原子、脂肪族低级酰基、取代或未取代的苯甲酰基；X和Y各自代表低级烷基；Z代表乙炔基或三低级烷基硅烷基乙炔基；式(1)中的糖基代表木糖；式(3)和(4)各自的糖基代表核糖)。本发明还涉及一种制备化合物（2）的工艺，其特征是在催化量的 2，2，6，6-四甲基哌啶氧基化合物存在下，用次氯酸盐氧化式（1）化合物。 这些化合物可作为合成 3'-C 取代的核糖核苷衍生物的中间体，具有优异的抗肿瘤活性。
• 2'-FLUORO-4'-SUBSTITUTED NUCLEOSIDES, THE PREPARATION AND USE
  申请人：Zhengzhou University

  公开号：EP2177527B1

  公开（公告）日：2013-12-18
• Nucleosides and nucleotides. Part 212: Practical large-scale synthesis of 1-(3-C-ethynyl-β-d-ribo-pentofuranosyl)cytosine (ECyd), a potent antitumor nucleoside. Isobutyryloxy group as an efficient anomeric leaving group in the Vorbrüggen glycosylation reaction
  作者：Makoto Nomura、Tsutomu Sato、Masato Washinosu、Motoaki Tanaka、Tetsuji Asao、Satoshi Shuto、Akira Matsuda

  DOI：10.1016/s0040-4020(01)01249-2

  日期：2002.2

  A practical synthetic route to the antitumor nucleoside, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd, 1) from 1,2-O-isopropylidene-D-xylofuranose (3) has been developed. Since most of the compounds were obtained as crystals, the target ECyd was prepared without any chromatographic purification in 31% overall yield from compound 3. The isobutyryloxy group was found to be an effective leaving group at the anomeric position of the 3-beta-C-ethynyl glycosyl donors in the key Vorbruggen glycosylation reaction. Using a similar procedure without chromatographic purification, the uracil congener EUrd [1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)uracil (2), which also has a potent antitumor effect, was synthesized from 3 in 39% overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.