methyl O-benzoyl-β-D-xylofuranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-benzoyl-β-D-xylofuranoside
• 英文别名: methyl 5-O-benzoyl-β-D-xylofuranoside；((2R,3R,4R,5R)-3,4-dihydroxy-5-methoxytetrahydrofuran-2-yl)methyl benzoate；5-O-benzoate methyl β-D-xylofuranoside；[(2R,3R,4R,5R)-3,4-dihydroxy-5-methoxyoxolan-2-yl]methyl benzoate
• 化学式: C₁₃H₁₆O₆
• 分子量: 268.266
• InChiKey: MCFYFVVNPNSYLK-LSCVPOLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	5-O-benzoyl-α-D-xylofuranose	6022-96-4	C15H18O6	294.304
  ——	methyl xylofuranoside	——	C6H12O5	164.158
  1,2-O-异亚丙基-alpha-D-呋喃木糖	1,2-O-isopropylidene-α-D-xylose	20031-21-4	C8H14O5	190.196

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	methyl 5-O-benzoyl-3-deoxy-3-fluoro-β-D-ribofuranoside	237410-10-5	C13H15FO5	270.258
  ——	methyl 5-O-benzoyl-3-deoxy-3-fluoro-α-D-ribofuranoside	237410-13-8	C13H15FO5	270.258
  ——	((2R,3R,4S,5R)-3-fluoro-4-hydroxy-5-methoxy-4-methyltetrahydrofuran-2-yl)methyl benzoate	1434144-23-6	C14H17FO5	284.284
  ——	((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-methoxy-4-methyltetrahydrofuran-2-yl)methyl benzoate	1434144-24-7	C14H17FO5	284.284

反应信息

• 作为反应物：
  描述：

  methyl O-benzoyl-β-D-xylofuranoside 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以710 mg的产率得到methyl 5-O-benzoyl-3-deoxy-3-fluoro-β-D-ribofuranoside
  参考文献：
  名称：

  [EN] SUBSTITUTED PURINE NUCLEOSIDES, PHOSPHORAMIDATE AND PHOSPHORDIAMIDATE DERIVATIVES FOR TREATMENT OF VIRAL INFECTIONS
  [FR] NUCLÉOSIDES DE PURINE SUBSTITUÉS, DÉRIVÉS PHOSPHORAMIDATE ET PHOSPHORDIAMIDATE DESTINÉS À TRAITER DES INFECTIONS VIRALES

  摘要：

  这项发明涉及具有结构的化合物（I）的公式，这些化合物在哺乳动物，特别是人类中，用于治疗由黄病毒科病毒介导的病毒感染。

  公开号：

  WO2013070887A1
• 作为产物：
  描述：

  1,2:3,5-双-O-异亚丙基-alpha-D-呋喃木糖 在 盐酸 、 硫酸 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.5h， 生成 methyl O-benzoyl-β-D-xylofuranoside
  参考文献：
  名称：

  3'-氟7-脱氮嘌呤核苷作为抗动素的合成与评价

  摘要：

  运动质体寄生虫是被忽视的热带病的病原体，医疗需求未得到满足。这些寄生虫无法从头合成嘌呤环，因此只能依靠嘌呤挽救来满足其嘌呤需求。因此，评价嘌呤核苷类似物是鉴定抗动素体药物的一种有吸引力的策略。几种抗克氏锥虫和抗布鲁氏锥虫先前已发现7-脱氮嘌呤核苷，并去除了3'-羟基，从而显着提高了活性。因此，在这项工作中，我们决定评估在7-脱氮嘌呤核苷中引入3'-氟取代基对抗动素体活性的影响。因此，我们合成了两个系列的3'-脱氧-3'- fluororibofuranosyl和3'-脱氧-3' - fluoroxylofuranosyl核苷包括7-脱氮腺嘌呤和次黄嘌呤碱，并测定这些对于抗寄生虫活性。发现了几种对克鲁斯氏锥虫和布鲁氏菌具有有效活性的类似物，表明3'-位的氟原子是发现抗寄生虫核苷的有前途的修饰。

  DOI：

  10.1016/j.ejmech.2021.113290

文献信息

• Synthesis of 2-fluoro-substituted and 2,6-modified purine 2′,3′-dideoxy-2′,3′-difluoro-d-arabinofuranosyl nucleosides from d-xylose
  作者：Grigorii G. Sivets、Franck Amblard、Raymond F. Schinazi

  DOI：10.1016/j.tet.2019.02.027

  日期：2019.3

  purine-modified 2′,3′-dideoxy-2′,3′-difluro-D-arabinonucleosides, including fluorinated analogs of fludarabine and nelarabine, have been prepared via anion glycosylation reactions of salts of 2-fluoropurine derivatives with the glycosyl bromide. A short and efficient synthetic route to the carbohydrate precursor 5-O-benzoyl-2,3-difluoro-α-d-arabinofuranosyl bromide was developed in five steps from d-xylose

  通过2-氟嘌呤衍生物与二氟嘌呤衍生物盐的阴离子糖基化反应，制备了一系列新型嘌呤修饰的2'，3'-二脱氧-2'，3'-二氟-D-阿拉伯糖核苷，包括氟达拉滨和奈拉拉滨的氟化类似物。糖基溴化物。从d-木糖分五个步骤开发了一种短而有效的合成方法，以合成碳水化合物前体5 - O-苯甲酰基-2,3-二氟-α - d-阿拉伯呋喃糖基溴。基于与5- O反应的二乙基氨基三氟化硫（DAST）反应的研究，改进了5- O-苯甲酰基-2,3-二氟-α - d-阿拉伯呋喃糖苷的合成在关键步骤上，使用温和的反应条件，研究了保护基保护的甲基D-木糖苷。据报道，用DAST选择性氟化5- O-苯甲酰化的α-和β-D-戊呋喃糖苷的新特性导致形成单和二氟呋喃糖苷衍生物。
• Substituted Purine Nucleosides, Phosphoramidate and Phosphordiamidate Derivatives for Treatment if Viral Infections
  申请人：INHIBITEX, INC.

  公开号：US20140286903A1

  公开（公告）日：2014-09-25

  This invention is directed to compounds of Formula (I) having the structure that are useful in the treatment of viral infections in mammals, particularly in humans, mediated, at least in part, by a virus in the Flaviviridae family of viruses.

  本发明涉及具有结构的I式化合物，其在哺乳动物，特别是人类中，对通过Flaviviridae病毒家族中的病毒介导的病毒感染的治疗中是有用的。
• A Novel Route for the Synthesis of Deoxy Fluoro Sugars and Nucleosides
  作者：Igor A. Mikhailopulo、Grigorii G. Sivets

  DOI：10.1002/(sici)1522-2675(19991110)82:11<2052::aid-hlca2052>3.0.co;2-7

  日期：1999.11.10

  The reaction of (diethylamino)sulfur trifluoride (DAST) with methyl 5-O-benzoyl-beta-D-xylofuranoside (1) followed by column chromatography afforded the riboside 2 (62%) and the ribo-epoxide 3 (18%) (Scheme 1). Under similar reaction conditions, the alpha-D-anomer 4 gave the riboside 5 and the difluoride 6 in 60 and 9% yield, respectively Treatment of the beta-D-xyloside 10 with DAST gave, after chromatographic purification, the riboside 11 as the principal product (48% 1 Scheme 2). These results suggest that the C(3)-O-SF2NEt2 derivatives were initially formed in the case of the xylosides studied. The distinctive feature of the reaction of DAST with the beta-D-arabinoside 12 consists in the formation of a 3- or 5-benzylideneoxoniumyl-substituted intermediate on one of the consecutive transformations, which finally give rise to the inversion of the configuration at C(3) affording the xylosides 17 (18%) and 18 (55% ): the lyxoside 14 was also isolated from the reaction mixture in a yield of 25% (Scheme 3). In the presence of the non-participating 5-O-trityl group, i.e.,from the reaction products of 21 with DAST. the compounds 23 and 23 were isolated in 16 and 52% yield, respectively (Scheme 4). It may be thus reasonable to conclude that, in the case of the beta-D-arabinosides 12 and 21, the principal route of the reaction is the formation of the intermediate C(2)-O-SF2NEt2 derivative. Unlike the alpha-D-arabinoside 26 was converted to the lyxo-epoxide 25 (53%) and the lyxoside 27 (14%), which implies the intermediate formation of the C(3)-O-SF2NEt2 derivative (Scheme 5).
• A Novel Route for the Synthesis of Fluorodeoxy Sugars and Nucleosides
  作者：Igor A. Mikhailopulo、Grigorii G. Sivets、Natalia B. Khripach

  DOI：10.1080/15257779908041542

  日期：1999.4

  Ring-fluorination of alpha- and beta-D-pentofuranosides containing free secondary hydroxyl groups by (diethylamino)sulfur trifluoride (DAST) was studied.
• SUBSTITUTED PURINE NUCLEOSIDES, PHOSPHORAMIDATE AND PHOSPHORDIAMIDATE DERIVATIVES FOR TREATMENT OF VIRAL INFECTIONS
  申请人：Inhibitex, Inc.

  公开号：EP2776438A1

  公开（公告）日：2014-09-17