2,3,5-tri-O-benzoyl-α-D-ribofuranosyl chloride | 50909-47-2

• 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: 2,3,5-tri-O-benzoyl-α-D-ribofuranosyl chloride
• 英文别名: (2R,3R,4R,5R)-2-((Benzoyloxy)methyl)-5-chlorotetrahydrofuran-3,4-diyl dibenzoate；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-chlorooxolan-2-yl]methyl benzoate
• CAS: 50909-47-2
• 化学式: C₂₆H₂₁ClO₇
• 分子量: 480.902
• InChiKey: RNPJWTDNQMCUHP-ODAXIHTASA-N

物化性质

• 沸点：
  607.6±55.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzoyl-α-D-ribofuranosyl chloride 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 54.0h， 生成 2-amino-9-(β-D-ribofuranosyl)-6-(trifluoromethyl)purine
  参考文献：
  名称：

  Synthesis and cytostatic activity of nucleosides and acyclic nucleoside analogues derived from 6-(trifluoromethyl)purines

  摘要：

  Glycosylation and alkylation of 6-(trifluoromethyl)purine by several protected halogenoses or hydroxyalkyl chlorides afforded regio- and stereoselectively the 9-beta-nucleosides or 9-alkylated purine derivatives in good yields. Deprotection of these intermediates gave a series of nucleoside (beta-D-ribofuranosyl, 2-deoxy-beta-D-ribofuranosyl and beta-D-arabinofuranosyl) and acyclonucleoside (2,3-dihydroxypropyl and (2-hydroxyethyl)oxymethyl) derivatives of 6-(trifluoromethyl)purine. While the ribofuranosyl derivative 1 showed significant cytostatic activity, the other derivatives were inactive. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00615-8
• 作为产物：
  描述：

  1-O-acetyl-2,3,5-tri-O-benzoyl-α-D-ribofuranose 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 168.0h， 生成 2,3,5-tri-O-benzoyl-α-D-ribofuranosyl chloride
  参考文献：
  名称：

  Improved Syntheses of Halofuranose Derivatives with the Desired α-Configuration

  摘要：

  AbstractChlorination of ribofuranose or 2‐deoxyribofuranose derivatives was carried out in a 1,4‐dioxane solution of hydrogen chloride. This improved procedure allowed the syntheses of 1‐chloro‐α‐D‐ribofuranose and 1‐chloro‐2‐deoxy‐α‐D‐ribofuranose derivatives and offered ease of handling, high yield, and the stereo‐controlled α‐configuration at C‐I.

  DOI：

  10.1002/jccs.199700062

文献信息

• A Novel, Simple Cyclocondensation Reaction Towards Glycosyl Triazines
  作者：David Deniaud、Vincent Kikelj、Karine Julienne、Pascal Janvier、Jean-Claude Meslin

  DOI：10.1055/s-0028-1083156

  日期：——

  Sugars bearing an isothiocyanate moiety at C-1 react with diazadienium iodide to afford glycosyl triazines that represent, through an easy cyclocondensation reaction step, a flexible entry to different nucleoside analogues. We herein demonstrate that this [4+2] cycloaddition reaction occurs with total regiocontrol and good yields. Subsequent transformation of the thiocarbonyl into a carbonyl, and nucleophilic substitution of the methylsulfanyl group by ammonia, yields the 5-azacytidine analogues. All compounds were fully characterised by IR, HRMS, and ¹³C and ¹H NMR (COSY­, HMBC and HMQC).

  在C-1位带有异硫氰酸基团的糖与二氮二烯丙碘反应生成糖基三嗪类化合物，这些化合物通过一步简单的环加成反应，提供了一种灵活的途径来制备不同的核苷类似物。我们在此证明，这种[4+2]环加成反应具有完全的区域选择性和良好的产率。随后将硫羰基转化为羰基，并通过氨对甲硫基进行亲核取代，得到了5-氮胞苷类似物。所有化合物均通过IR、HRMS以及¹³C和¹H NMR（包括COSY、HMBC和HMQC）进行了全面的表征。
• Adenosine Analogs and Their Use
  申请人：Ben-Zeev Efrat

  公开号：US20110237529A1

  公开（公告）日：2011-09-29

  The invention provides adenosine analog compounds that act at P2Y receptors, e.g., the P2Y 2 receptor, including pharmaceutical compositions; and uses thereof to treat or prevent diseases associated with that receptor, e.g., disorders relating to mucus secretion, such as cystic fibrosis, chronic obstructive pulmonary disorder (COPD), asthma, constipation, chronic idiopathic constipation, dry mouth (xerostomia), gum disease, and gastrointestinal problems caused by radiation and chemotherapy for cancer.

  该发明提供了在P2Y受体上起作用的腺苷类似化合物，例如P2Y2受体，包括药物组合物；以及将其用于治疗或预防与该受体相关的疾病，例如与粘液分泌有关的疾病，如囊性纤维化、慢性阻塞性肺病（COPD）、哮喘、便秘、慢性特发性便秘、口干（口腔干燥症）、牙龈疾病，以及由放射治疗和化疗引起的癌症的胃肠道问题。
• [EN] IMPROVED SYNTHESIS OF 2-SUBSTITUTED ADENOSINES<br/>[FR] SYNTHESE AMELIOREE D'ADENOSINES SUBSTITUEES EN 2
  申请人：CAMBRIDGE BIOTECHNOLOGY LTD

  公开号：WO2005056571A1

  公开（公告）日：2005-06-23

  Synthesis of 2-substituted adenosines of formula (I) using 2-nitro pentabenzoyl adenosine, or 2-nitro pentaacetyl adenosine, as intermediate is described: Formula (I) wherein R = C1-6 alkoxy (straight or branched), a phenoxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, C1-6 alkyl, or C1-6 alkoxy), a benzyloxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, C1-6 alkyl, or C1-6 alkoxy), or a benzoyl group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-,cyano, nitro, C1-6 alkyl, or C1-6 alkoxy). The methods provide improved yield and purity of product.

  使用2-硝基戊二酰基腺苷或2-硝基戊醋酰基腺苷作为中间体，描述了合成式(I)的2-取代腺苷的方法：式(I)中，R = C1-6烷氧基（直链或支链）、苯氧基（未取代或经氯、氨基、三氟甲基、氰基、硝基、C1-6烷基或C1-6烷氧基单取代或双取代）、苄氧基（未取代或经氯、氨基、三氟甲基、氰基、硝基、C1-6烷基或C1-6烷氧基单取代或双取代）、或苯甲酰基（未取代或经氯、氨基、三氟甲基、氰基、硝基、C1-6烷基或C1-6烷氧基单取代或双取代）。该方法提供了改善产物产量和纯度的效果。
• Synthesis of 5-azacytidine
  申请人：——

  公开号：US20040186283A1

  公开（公告）日：2004-09-23

  The present invention provides a method for the preparation of 5-azacytidine, wherein 5-azacytidine is represented by the structure: 1 The method involves the silylation of 5-azacytosine, followed by the coupling of silylated 5-azacytosine to a protected &bgr;-D-ribofuranose derivative. The coupling reaction is catalyzed by trimethylsilyl trifluoromethanesulfonate (TMS-Triflate).

  本发明提供了一种制备5-氮杂胞嘧啶的方法，其中5-氮杂胞嘧啶的结构如下：1该方法涉及对5-氮杂胞嘧啶进行硅烷基化，然后将硅烷基化的5-氮杂胞嘧啶与受保护的β-D-核糖呋喃糖衍生物进行偶联。偶联反应由三甲基硅酰基三氟甲磺酸酯（TMS-Triflate）催化。
• [EN] IMPROVED SYNTHESIS OF 2-SUBSTITUTED ADENOSINES<br/>[FR] SYNTHESE AMELIOREE D'ADENOSINES 2-SUBSTITUEES
  申请人：CAMBRIDGE BIOTECHNOLOGY LTD

  公开号：WO2005054269A1

  公开（公告）日：2005-06-16

  A method of synthesis of a 2-substituted adenosine of formula I which comprises converting a compound of formula II to a compound of formula (I), wherein: R is C 1-6 alkoxy (straight or branched), a phenoxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, C 1-6 alkyl, or C 1-6 alkoxy), a benzyloxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, Cl_6 alkyl, or Cl_6 alkoxy), or a benzoyl group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, C 1-6 alkyl, or C 1-6 alkoxy); R' = H, or a protecting group.

  一种合成式I的2-取代腺苷的方法，包括将式II的化合物转化为式(I)的化合物，其中：R为C 1-6烷氧基（直链或支链）、苯氧基（未取代或经氟、氨基、CF3-、氰基、硝基、C 1-6烷基或C 1-6烷氧基单取代或双取代）、苄氧基（未取代或经氟、氨基、CF3-、氰基、硝基、Cl_6烷基或Cl_6烷氧基单取代或双取代）或苯甲酰基（未取代或经氟、氨基、CF3-、氰基、硝基、C 1-6烷基或C 1-6烷氧基单取代或双取代）；R' = H或保护基。