2,3,5-tetra-O-benzoyl-α-D-arabinofuranosyl chloride | 59599-14-3

• 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-tetra-O-benzoyl-α-D-arabinofuranosyl chloride
• 英文别名: 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl chloride；(2R,3R,4S,5R)-2-((Benzoyloxy)methyl)-5-chlorotetrahydrofuran-3,4-diyl dibenzoate；[(2R,3R,4S,5R)-3,4-dibenzoyloxy-5-chlorooxolan-2-yl]methyl benzoate
• CAS: 59599-14-3
• 化学式: C₂₆H₂₁ClO₇
• 分子量: 480.902
• InChiKey: RNPJWTDNQMCUHP-LUKWVAJMSA-N

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-tetra-O-benzoyl-α-D-arabinofuranosyl chloride 在 四丁基溴化铵 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 β-D-arabinofuranose 1,2,5-orthobenzoate
  参考文献：
  名称：

  Ring opening of acylated β-d-arabinofuranose 1,2,5-orthobenzoates with nucleophiles allows access to novel selectively-protected arabinofuranose building blocks

  摘要：

  beta-D-Arabinofuranose 1,2,5-orthobenzoates with 3-O-acetyl, 3-O-benzoyl, and 3-O-chloroacetyl groups were prepared in an efficient manner starting from readily available crystalline methyl 2,3,5-tri-O-benzoyl-alpha-D-arabinofuranoside, and ring-opening reactions of these compounds with O- and S-nucleophiles were studied. Optimized conditions leading to the formation of the respective monosaccharide adducts (up to 96% isolated yields) and to alpha-(1 -> 5)-linked disaccharide thioglycosides with 5'-OH unprotected (up to 30% isolated yields) were found. Basing on these results, a novel approach for effective differentiation of 3,5-diol system and 2-hydroxy group in arabinofuranose thioglycosides was proposed. The selectively protected derivatives prepared are valuable building blocks for the assembly of linear and branched oligoarabinofuranosides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.11.002
• 作为产物：
  描述：

  methyl tri-O-benzoyl-α-D-arabinofuranoside 在 盐酸 、 溶剂黄146 作用下， 反应 0.83h， 以63%的产率得到2,3,5-tetra-O-benzoyl-α-D-arabinofuranosyl chloride
  参考文献：
  名称：

  Synthesis and Antiviral Properties of Arabino and Ribonucleosides of 1,3‐Dideazaadenine, 4‐Nitro‐1, 3‐dideazaadenine and Diketopiperazine

  摘要：

  Different arabinosides and ribosides, viz. Ara-DDA or 9(1-beta-(D)-arabinofuranosyl) 1,3-dideazaadenine (6), Ara-NDDP or 9(1-beta-D-arabinofuranosyl) 4-nitro-1,3-dideazapurine (7), Ara-DKP or I(1-beta-D-arabinofuranosyl) diketopiperazine (8), Ribo-DDA or 9(1-beta-D-ribofuranosyl) 1,3-dideazaadenine (9) and Ribo-NDDP or 9(1-beta-D-ribofuranosyl) 4-nitro-1,3-dideazapurine (10) have been synthesized as probable antiviral agents. The arabinosides have been synthesized using the catalyst TDA-1 that causes stereospecific formation of beta-nucleosides while a one-pot synthesis procedure was adopted for the synthesis of the ribonucleosides where beta-anomers were obtained in higher yields. All the five nucleoside analogs have been screened for antiviral property against HIV-1 ((IIIB)), HSV-1 and 2, parainfluenza-3, reovirus-1 and many others. It was observed that arabinosides had greater inhibitory action than ribosides. The compound 7 or Ara-NDDP has shown maximum inhibition of HIV-1 replication than the rest of the molecules with an IC50 of 79.4 mug/mL.

  DOI：

  10.1081/ncn-200040614

文献信息

• Synthesis and antibacterial activity of ricinoleic acid glycosides
  作者：Ramakrishna Kuppala、Mugunthan Govindarajan、Rushikesh Tambat、Neeraj Patel、Hemraj Nandanwar、Kamlesh K. Bhutani、K. P. Ravindranathan Kartha

  DOI：10.1039/c5ra20136e

  日期：——

  The antibacterial properties of twenty-eight novel ricinoleic acid glycosides synthesized by Koenigs–Knorr glycosylation are reported.

  报道了由Koenigs-Knorr糖基化合成的二十八种新型蓖麻油酸糖苷的抗菌性能。
• Synthesis and Antiviral Properties of Arabino and Ribonucleosides of 1,3‐Dideazaadenine, 4‐Nitro‐1, 3‐dideazaadenine and Diketopiperazine
  作者：Sarika Sinha、Richa Srivastava、Erik De Clercq、Ramendra K. Singh

  DOI：10.1081/ncn-200040614

  日期：2004.1.12

  Different arabinosides and ribosides, viz. Ara-DDA or 9(1-beta-(D)-arabinofuranosyl) 1,3-dideazaadenine (6), Ara-NDDP or 9(1-beta-D-arabinofuranosyl) 4-nitro-1,3-dideazapurine (7), Ara-DKP or I(1-beta-D-arabinofuranosyl) diketopiperazine (8), Ribo-DDA or 9(1-beta-D-ribofuranosyl) 1,3-dideazaadenine (9) and Ribo-NDDP or 9(1-beta-D-ribofuranosyl) 4-nitro-1,3-dideazapurine (10) have been synthesized as probable antiviral agents. The arabinosides have been synthesized using the catalyst TDA-1 that causes stereospecific formation of beta-nucleosides while a one-pot synthesis procedure was adopted for the synthesis of the ribonucleosides where beta-anomers were obtained in higher yields. All the five nucleoside analogs have been screened for antiviral property against HIV-1 ((IIIB)), HSV-1 and 2, parainfluenza-3, reovirus-1 and many others. It was observed that arabinosides had greater inhibitory action than ribosides. The compound 7 or Ara-NDDP has shown maximum inhibition of HIV-1 replication than the rest of the molecules with an IC50 of 79.4 mug/mL.
• HASAN, A.;TRIPATHI, R. P.;PRATAP, RAM;BHAKUNI, D. S.;PAL, R.;MISHRA, A.;G+, INDIAN J. CHEM. B , 28,(1989) N, C. 403-409
  作者：HASAN, A.、TRIPATHI, R. P.、PRATAP, RAM、BHAKUNI, D. S.、PAL, R.、MISHRA, A.、G+

  DOI：——

  日期：——
• Ring opening of acylated β-d-arabinofuranose 1,2,5-orthobenzoates with nucleophiles allows access to novel selectively-protected arabinofuranose building blocks
  作者：Nikita M. Podvalnyy、Sergey L. Sedinkin、Polina I. Abronina、Alexander I. Zinin、Ksenia G. Fedina、Vladimir I. Torgov、Leonid O. Kononov

  DOI：10.1016/j.carres.2010.11.002

  日期：2011.1

  beta-D-Arabinofuranose 1,2,5-orthobenzoates with 3-O-acetyl, 3-O-benzoyl, and 3-O-chloroacetyl groups were prepared in an efficient manner starting from readily available crystalline methyl 2,3,5-tri-O-benzoyl-alpha-D-arabinofuranoside, and ring-opening reactions of these compounds with O- and S-nucleophiles were studied. Optimized conditions leading to the formation of the respective monosaccharide adducts (up to 96% isolated yields) and to alpha-(1 -> 5)-linked disaccharide thioglycosides with 5'-OH unprotected (up to 30% isolated yields) were found. Basing on these results, a novel approach for effective differentiation of 3,5-diol system and 2-hydroxy group in arabinofuranose thioglycosides was proposed. The selectively protected derivatives prepared are valuable building blocks for the assembly of linear and branched oligoarabinofuranosides. (C) 2010 Elsevier Ltd. All rights reserved.