methyl 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α-D-arabinofuranoside | 237410-14-9

• 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: methyl 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α-D-arabinofuranoside
• 英文别名: [(2R,3R,4R,5S)-3,4-difluoro-5-methoxyoxolan-2-yl]methyl benzoate
• CAS: 237410-14-9
• 化学式: C₁₃H₁₄F₂O₄
• 分子量: 272.249
• InChiKey: BVQYXLNOQNZXPO-DCQANWLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：
  44.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α-D-arabinofuranoside 在 氢溴酸 、 乙酸酐 、 溶剂黄146 作用下， 反应 18.0h， 以50%的产率得到methyl 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α,β-D-arabinofuranose
  参考文献：
  名称：

  由d-木糖合成2-氟取代和2,6-修饰的嘌呤2'，3'-二脱氧-2'，3'-二氟-d-阿拉伯呋喃糖基核苷

  摘要：

  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。

  DOI：

  10.1016/j.tet.2019.02.027
• 作为产物：
  描述：

  methyl 5-O-benzoyl-3-deoxy-3-fluoro-2-O-(imidazol-2-ylsulfonyl)-α-D-ribofuranoside 在 potassium hydrogen bifluoride 、 氢氟酸 作用下， 以 水 、 2,3-丁二醇 为溶剂， 反应 0.83h， 以49%的产率得到methyl 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-α-D-arabinofuranoside
  参考文献：
  名称：

  嘌呤 2',3'-Dideoxy-2',3'-Difluoro-D-Arabinofuranosyl Nucleosides 的合成及抗病毒活性

  摘要：

  9-(2',3'-Dideoxy-2',3'-difluoro-β-D-arabinofuranosyl)adenine (20), 2-chloro-9-(2',3'-dideoxy-2,3-difluoro -β-D-arabinofuranosyl)adenine (22) 以及它们各自的 α-anomers 21 和 23，是通过中间体 5-O-benzoyl-2,3-dideoxy-2,3-difluoro 的核碱基阴离子糖基化合成的-α-D-阿拉伯呋喃糖基溴化物 (13) 从甲基 5-O-benzyl-3-deoxy-3-fluoro-α-D-ribofuranoside (3) 和甲基 5-O-benzoyl-α-D-xylofuranoside (10) 开始）。这些化合物分别被评估为人类 PBM 和 Huh-7 Replicon 细胞中 HIV-1 和丙型肝炎病毒的潜在抑制剂。腺苷类似物

  DOI：

  10.1080/15257770903053979

文献信息

• Synthesis and antiviral evaluation of 2′,3′-dideoxy-2′,3′-difluoro-D-arabinofuranosyl 2,6-disubstituted purine nucleosides
  作者：Raymond F. Schinazi、Grigorii G. Sivets、Mervi A. Detorio、Tami R. McBrayer、Tony Whitaker、Steven J. Coats、Franck Amblard

  DOI：10.1515/hc-2015-0174

  日期：2015.10.1

  Abstract The synthesis of new 2,6-disubstituted purine 2′,3′-dideoxy-2′,3′-difluoro-D-arabino nucleosides is reported. Their ability to block HIV and HCV replication along with their cytotoxicity toward Huh-7 cells, human lymphocyte, CEM and Vero cells was also assessed. Among them, β-2,6-diaminopurine nucleoside 25 and guanosine derivative 27 demonstrate potent anti-HIV-1 activity (EC50 = 0.56 and

  摘要 报道了新的 2,6-二取代嘌呤 2',3'-dideoxy-2',3'-difluoro-D-arabino 核苷的合成。还评估了它们阻断 HIV 和 HCV 复制的能力以及它们对 Huh-7 细胞、人淋巴细胞、CEM 和 Vero 细胞的细胞毒性。其中，β-2,6-二氨基嘌呤核苷 25 和鸟苷衍生物 27 表现出有效的抗 HIV-1 活性（EC50 = 0.56 和 0.65 μm；EC90 = 4.2 和 3.1 μm），同时在原代人类淋巴细胞中仅显示中等细胞毒性。
• Synthesis of 9-(2,3-Dideoxy-2,3-Difluoro-β-D- Arabinofuranosyl)Adenine
  作者：Grigorii G. Sivets、Elena N. Kalinichenko、Igor A. Mikhailopulo

  DOI：10.1080/15257770701534063

  日期：2007.11.26

  Convergent synthesis of 9-(2,3-dideoxy-2,3-difluoro-beta-D-arabinofuranosyl)adenine is described starting from methyl 5-O-benzyl-2-deoxy-2-fluoro-alpha-D-arabinofuranoside.

  描述了从5-O-苄基-2-脱氧-2-氟-2-氟-α-D-呋喃糖苷甲基开始聚合合成9-（2,3-二脱氧-2,3-二氟-β-D-阿拉伯呋喃糖基）腺嘌呤。
• 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.
• PREPARATION AND METHODS OF USE FOR ORTHO-ARYL 5-MEMBERED HETEROARYL-CARBOXAMIDE CONTAINING MULTI-TARGETED KINASE INHIBITORS
  申请人：Spacefill Enterprises LLC

  公开号：US20160303128A1

  公开（公告）日：2016-10-20

  The present disclosure relates to compounds of the Formula (I): and pharmaceutically acceptable salts, as kinase modulators, compatible with the Type-II inhibition of kinases.