methyl 3,5-di-O-(4-chlorobenzoyl)-2-deoxy-D-erythro-pentofuranoside

• 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: methyl 3,5-di-O-(4-chlorobenzoyl)-2-deoxy-D-erythro-pentofuranoside
• 英文别名: 1-O-methyl-3,5-bis-O-p-chlorobenzoyl-2-deoxy-D-furanoside；methyl 2-deoxy-3,5-di-O-(p-chlorobenzoyl)-D-ribofuranoside；1-Methoxy-3,5-Bis-(4-chlorobenzoyl)-2-Deoxy-D-Ribose；[(2R,3S)-3-(4-chlorobenzoyl)oxy-5-methoxyoxolan-2-yl]methyl 4-chlorobenzoate
• 化学式: C₂₀H₁₈Cl₂O₆
• 分子量: 425.265
• InChiKey: RDJPJXIHFSQOKW-MYFVLZFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 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
  1-氯-2-脱氧-3,5-二-O-对氯苯甲酰基-D-核糖	3,5-O-bis(4-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride	21740-23-8	C19H15Cl3O5	429.684

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2-deoxy-3,5-di-O-(p-chlorobenzoyl)-γ-D-ribonolactone	——	C19H14Cl2O6	409.223
  1-氯-3,5-二对氯苯甲酰氧基-2-脱氧-D-核糖	5-chloro-2-(((4-chlorobenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-chlorobenzoate	3601-90-9	C19H15Cl3O5	429.684

反应信息

• 作为反应物：
  描述：

  methyl 3,5-di-O-(4-chlorobenzoyl)-2-deoxy-D-erythro-pentofuranoside 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 20.0h， 生成 1-氯-3,5-二对氯苯甲酰氧基-2-脱氧-D-核糖
  参考文献：
  名称：

  立体固定的溴movylyl尿嘧啶：呋喃[2,3- d ]嘧啶核苷的合成

  摘要：

  报道了一种合成5,6-二氢呋喃并[2,3- d ]嘧啶-2（3 H）-one（3）及其脱氧核糖核苷8的新方法。化合物3与各种试剂进行亲核反应以产生5-取代的尿嘧啶衍生物。BVU 15的环化反应合成了3，furo [2,3- d ]嘧啶-2（3 H）-one（18）的脱氢衍生物，这为开发BV（ D）U 从18开始，α-脱氧核糖核苷20和β-核糖核苷22 准备好了。

  DOI：

  10.1002/jhet.5570320135
• 作为产物：
  描述：

  2-脱氧-D-核糖 在 盐酸 、 三乙胺 作用下， 以 丙酮 为溶剂， 反应 10.0h， 生成 methyl 3,5-di-O-(4-chlorobenzoyl)-2-deoxy-D-erythro-pentofuranoside
  参考文献：
  名称：

  一种地西他滨的合成方法

  摘要：

  本发明涉及一种地西他滨的合成方法，公开了一种如式I所示的化合物的合成方法，其包括如下步骤：在溶剂中，在TMSOTf的作用下，将化合物II与化合物III进行如下所示的反应得到化合物I即可；本发明的合成方法具有原料易得，操作安全，条件温和、易控，且酰化保护后得到的固体产物易结晶提纯，有利于下步反应和提高最终β‑异构体产物的选择性，不需要对羟基甲基做进一步的转化，反应步骤得到了简化，各步反应收率好，原子经济性高，适合大量工业化生产等优点。

  公开号：

  CN110028537A

文献信息

• 一种合成地西他滨中间体的方法
  申请人：连云港恒运药业有限公司

  公开号：CN110655540A

  公开（公告）日：2020-01-07

  本发明涉及一种合成地西他滨中间体的方法。本发明涉及一种如式二所示结构的地西他滨中间体合成方法，该方法能够极大提高此类中间体纯度，从而减少地西他滨的纯化操作，首次成功分离出过渡态中间体化合物，将制备地西他滨的总收率提高3倍。
• Stereoselective synthesis of 1,2-cis- and 2-deoxyglycofuranosyl azides from glycosyl halides
  作者：Anton Štimac、Jože Kobe

  DOI：10.1016/s0008-6215(00)00186-5

  日期：2000.11

  2-deoxy-2-fluoro-beta-D-arabino configurations were efficiently prepared from the appropriate 1,2-trans glycosyl halides bearing non-participating 0-2 substituent by inversion with sodium azide under phase transfer catalytic conditions (80-85% yields, 90-96% de). The same method failed to result in sufficiently good beta-selectivity starting from 2-deoxy-3,5-di-O-(p-toluoyl)-alpha-D-ery-thro-pentofuranosyl chloride

  从具有1,2-三氟-β-阿拉伯糖基构型的合适的1,2-反式糖基卤化物有效地制备具有α-D-核糖，β-D-阿拉伯糖基和2-脱氧-2-氟-β-D-阿拉伯糖基构型的受保护的1,2-顺式呋喃呋喃糖基叠氮化物。 -在相转移催化条件下，通过叠氮化钠的转化使-参与0-2取代基-转化（80-85％产率，90-96％de）。从2-deoxy-3,5-di-O-（p-toluoyl）-alpha-D-ery-thro-pent呋喃呋喃糖酰氯（5alpha）（40％de）开始，相同的方法未能导致足够好的β-选择性。通过在室温下在二甲基亚砜中用铯或叠氮化钾处理5α及其对氯苯甲酰基类似物6α，大大提高了保护被保护的2-脱氧-β-D-赤型五氟呋喃糖基-叠氮基的选择性（74-80％de）温度（83-85％产率）。
• 2-FLUORINATED RIBOSES AND ARABINOSES AND METHODS OF USE AND SYNTHESIS
  申请人：Sauve Anthony A.

  公开号：US20120108535A1

  公开（公告）日：2012-05-03

  Disclosed are halogenated 2-deoxy-lactone, 2′-deoxy-nucleosides, and derivatives thereof, for example, a compound of formula (I). Also disclosed are a composition comprising a pharmaceutically acceptable carrier and at least one compound or salt of the invention, and a method of treating a disorder is selected from the group consisting of an abnormal cellular proliferation, a viral infection, and an autoimmune disorder.

  本发明涉及卤代的2-去氧内酯，2'-去氧核苷以及它们的衍生物，例如，化合物式（I）的化合物。本发明还涉及一种包含药学上可接受的载体和至少一种本发明化合物或盐的组合物，以及一种治疗异常细胞增殖、病毒感染和自身免疫性疾病等疾病的方法。
• [EN] HALOGENATED 2-DEOXY-LACTONES, 2'-DEOXY--NUCLEOSIDES, AND DERIVATIVES THEREOF<br/>[FR] 2-DÉSOXY-LACTONES HALOGÉNÉES, 2'-DÉSOXY-NUCLÉOSIDES, ET LEURS DÉRIVÉS
  申请人：UNIV CORNELL

  公开号：WO2011003018A9

  公开（公告）日：2012-11-08
• Diastereocontrolled Electrophilic Fluorinations of 2-Deoxyribonolactone: Syntheses of All Corresponding 2-Deoxy-2-fluorolactones and 2′-Deoxy-2′-fluoro-NAD⁺s
  作者：Yana Cen、Anthony A. Sauve

  DOI：10.1021/jo900637f

  日期：2009.8.21

  Methods to construct 2'-deoxy-2'-fluoro nucleosides have undergone limited improvement in the last 20 years in spite of the substantially increased value of these compounds as pharmaceuticals and as tools for studying biological processes. We herein describe a consolidated approach to synthesize precursors to these commercially and scientifically valuable compounds via diastereocontrolled fluorination of the readily available precursor 2-deoxy-D-ribonolactone. With employment of appropriate sterically bulky silyl protecting groups at the 3 and 5 positions, controlled electrophilic fluorination of the Li-ribonolactone enolate by N-fluorodibenzenesulfonamide yielded the corresponding 2-deoxy-2-fluoroarabinolactone in high isolated yield (72%) The protected 2-deoxy-2,2-difluororibonolactone was obtained similarly in high yield from a second round of electrophilic fluorination (two steps, 51% from protected ribonolactone starting material). Accomplishment of the difficult ribofluorination of the lactone was achieved by the directive effects of a diastereoselectively installed (x-trimethylsilyl group. Electrophilic fluorination of a protected 2-deoxy-2-trimethylsilylarabinolactone via enolate generation provided the protected 2-deoxy-2-fluororibolactone as the exclusive fluorinated product. The reaction also yielded the starting material, the desilylated protected 2-deoxyribonolactone, which was recycled to provide a 38% chemical yield of the fluorinated product (versus initial protected ribonolactone),after consecutive silylation and fluorination cycles. Using our fluorinated sugar precursors, we prepared the 2'-fluoroarabino-, 2'-fluororibo-, and 2',2'-difluoronicotinamide adenine dinucleotides (NAD(+)) of potential biological interest. These syntheses provide the most consolidated and efficient methods for production of sugar precursors of 2'-deoxy-2'-fluoronucleosides and have the advantage of utilizing an air-stable electrophilic fluorinating agent. The fluorinated NAD(+)s are anticipated to be useful for studying a variety of cellular metabolic and signaling processes.