2,3,4,5-tetra-O-benzyl-D-arabinonamide | 216772-11-1

• 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: 2,3,4,5-tetra-O-benzyl-D-arabinonamide
• 英文别名: (2S,3R,4R)-2,3,4,5-tetrakis(phenylmethoxy)pentanamide
• CAS: 216772-11-1
• 化学式: C₃₃H₃₅NO₅
• 分子量: 525.645
• InChiKey: WAXHTWICECEXDR-IWWXRALLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3,4,5-tetra-O-benzyl-D-arabinonamide 在 palladium dihydroxide 三甲基溴硅烷 、 potassium tert-butylate 、 水 、 氢气 作用下， 以 水 、 叔丁醇 为溶剂， 25.0~50.0 ℃ 、1000.0 kPa 条件下， 反应 158.08h， 生成 N-(2,2-diphosphonoethyl)-D-arabinonamide
  参考文献：
  名称：

  N-Monoalkylation of Tetra-O-benzyl-D-arabinonamide: Synthesis of Some Open-Chain Analogues ofN-Acetylneuraminic Acid and Their Evaluation as Sialidase Inhibitors

  摘要：

  N-Arabinonoylglycine 2, its phospho analogue (arabinonoylamino)methylphosphonate 14, N-arabinonoyltaurine salt 18, and [2-(arabinonoylamino)ethylidene]bis[phosphonic acid] 22 have been synthesized from D-arabinose in seven (2 or 14), and eight steps (18 or 22a), respectively. With the exception of the salt 22b, none of these compounds showed a significant inhibitory activity in vitro against the sialidases of Vibrio cholerae, Salmonella typhimurium, or Influenza A (N9), or B (B/Lee/40) virus. Ammonolysis of the oxosulfonate 8 obtained by oxidation of the hydrogensulfite adduct 7 of 2,3,4,5-tetra-O-benzyl-aldehydo-D-arabinose (6) yielded the primary amide 9 (64% from 6),which was alkylated with the triflates 10 or 11 of benzyl glycolate and dibenzyl hydroxymethylphosphonate, respectively, to give the protected N-arabinonoylglycinate 12 and the (arabinonoylamino)methylphosphonate 13 (45 and 90%, resp.), N-Alkylation of 9 with 2-bromoethyl triflate 15 followed by nucleophilic displacement with sodium sulfite yielded the protected taurine analogue 17 (21% from 9), whereas the protected tetraethyl bis[phosphonate] 20 was formed in 90% yield by 1,4-addition of 9 to tetraethyl ethenylidenebis[phosphonate] 19. Debenzylation of 12 and 13, followed by purification by reversed-phase HPLC gave the triethylammonium salt of N-(D-arabinonoyl)glycine (2) and triethylammonium (D-arabinonoylamino)methylphosphonate (14b), respectively, whereas the deprotection of 17 afforded the N-(D-arabinonoyl)taurine salt 18. Debenzylation of 20, followed by treatment with Me3SiBr and hydrolysis of the resulting silyl ester gave the bis[phosphonic acid] 22a (3 steps, 88%).

  DOI：

  10.1002/(sici)1522-2675(19981007)81:10<1896::aid-hlca1896>3.0.co;2-5
• 作为产物：
  描述：

  D-arabinose diethyl dithioacetal 在 sodium hydroxide 、 二氧化硫 、 氨 、 乙酸酐 、 四丁基碘化铵 、 sodium hydride 、 二甲基亚砜 、 calcium carbonate 、 mercury dichloride 作用下， 以 乙醚 、 水 、 乙腈 为溶剂， 反应 110.0h， 生成 2,3,4,5-tetra-O-benzyl-D-arabinonamide
  参考文献：
  名称：

  N-Monoalkylation of Tetra-O-benzyl-D-arabinonamide: Synthesis of Some Open-Chain Analogues ofN-Acetylneuraminic Acid and Their Evaluation as Sialidase Inhibitors

  摘要：

  N-Arabinonoylglycine 2, its phospho analogue (arabinonoylamino)methylphosphonate 14, N-arabinonoyltaurine salt 18, and [2-(arabinonoylamino)ethylidene]bis[phosphonic acid] 22 have been synthesized from D-arabinose in seven (2 or 14), and eight steps (18 or 22a), respectively. With the exception of the salt 22b, none of these compounds showed a significant inhibitory activity in vitro against the sialidases of Vibrio cholerae, Salmonella typhimurium, or Influenza A (N9), or B (B/Lee/40) virus. Ammonolysis of the oxosulfonate 8 obtained by oxidation of the hydrogensulfite adduct 7 of 2,3,4,5-tetra-O-benzyl-aldehydo-D-arabinose (6) yielded the primary amide 9 (64% from 6),which was alkylated with the triflates 10 or 11 of benzyl glycolate and dibenzyl hydroxymethylphosphonate, respectively, to give the protected N-arabinonoylglycinate 12 and the (arabinonoylamino)methylphosphonate 13 (45 and 90%, resp.), N-Alkylation of 9 with 2-bromoethyl triflate 15 followed by nucleophilic displacement with sodium sulfite yielded the protected taurine analogue 17 (21% from 9), whereas the protected tetraethyl bis[phosphonate] 20 was formed in 90% yield by 1,4-addition of 9 to tetraethyl ethenylidenebis[phosphonate] 19. Debenzylation of 12 and 13, followed by purification by reversed-phase HPLC gave the triethylammonium salt of N-(D-arabinonoyl)glycine (2) and triethylammonium (D-arabinonoylamino)methylphosphonate (14b), respectively, whereas the deprotection of 17 afforded the N-(D-arabinonoyl)taurine salt 18. Debenzylation of 20, followed by treatment with Me3SiBr and hydrolysis of the resulting silyl ester gave the bis[phosphonic acid] 22a (3 steps, 88%).

  DOI：

  10.1002/(sici)1522-2675(19981007)81:10<1896::aid-hlca1896>3.0.co;2-5

文献信息

• N-Monoalkylation of Tetra-O-benzyl-D-arabinonamide: Synthesis of Some Open-Chain Analogues ofN-Acetylneuraminic Acid and Their Evaluation as Sialidase Inhibitors
  作者：Thomas Storz、Andrea Vasella

  DOI：10.1002/(sici)1522-2675(19981007)81:10<1896::aid-hlca1896>3.0.co;2-5

  日期：1998.10.7

  N-Arabinonoylglycine 2, its phospho analogue (arabinonoylamino)methylphosphonate 14, N-arabinonoyltaurine salt 18, and [2-(arabinonoylamino)ethylidene]bis[phosphonic acid] 22 have been synthesized from D-arabinose in seven (2 or 14), and eight steps (18 or 22a), respectively. With the exception of the salt 22b, none of these compounds showed a significant inhibitory activity in vitro against the sialidases of Vibrio cholerae, Salmonella typhimurium, or Influenza A (N9), or B (B/Lee/40) virus. Ammonolysis of the oxosulfonate 8 obtained by oxidation of the hydrogensulfite adduct 7 of 2,3,4,5-tetra-O-benzyl-aldehydo-D-arabinose (6) yielded the primary amide 9 (64% from 6),which was alkylated with the triflates 10 or 11 of benzyl glycolate and dibenzyl hydroxymethylphosphonate, respectively, to give the protected N-arabinonoylglycinate 12 and the (arabinonoylamino)methylphosphonate 13 (45 and 90%, resp.), N-Alkylation of 9 with 2-bromoethyl triflate 15 followed by nucleophilic displacement with sodium sulfite yielded the protected taurine analogue 17 (21% from 9), whereas the protected tetraethyl bis[phosphonate] 20 was formed in 90% yield by 1,4-addition of 9 to tetraethyl ethenylidenebis[phosphonate] 19. Debenzylation of 12 and 13, followed by purification by reversed-phase HPLC gave the triethylammonium salt of N-(D-arabinonoyl)glycine (2) and triethylammonium (D-arabinonoylamino)methylphosphonate (14b), respectively, whereas the deprotection of 17 afforded the N-(D-arabinonoyl)taurine salt 18. Debenzylation of 20, followed by treatment with Me3SiBr and hydrolysis of the resulting silyl ester gave the bis[phosphonic acid] 22a (3 steps, 88%).