(2R,3S,4R,5R)-3-Benzyloxy-5-[(4-methoxy-benzylamino)-methyl]-hexane-1,2,4,6-tetraol | 791067-01-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R)-3-Benzyloxy-5-[(4-methoxy-benzylamino)-methyl]-hexane-1,2,4,6-tetraol
• CAS: 791067-01-1
• 化学式: C₂₂H₃₁NO₆
• 分子量: 405.491
• InChiKey: NJRBNOHBSHPLJL-ZHHKINOHSA-N

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R)-3-Benzyloxy-5-[(4-methoxy-benzylamino)-methyl]-hexane-1,2,4,6-tetraol 在 palladium on activated charcoal sodium periodate 、 氢气 、 sodium carbonate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 39.0h， 生成 4-[N-(tert-butyloxycarbonyl)-N-(p-methoxybenzyl)amino]methyl-4-deoxy-β-D-arabinopyranose
  参考文献：
  名称：

  Synthesis and Chemistry of Noeuromycin and Isofagomine Analogues

  摘要：

  Several N-substituted analogues of noeuromycin ((2RS,3S,4R,5R)-2,3,4-trihydroxy-5 -hydroxymethylpiperidine) and isofagomine ((3R,4R,5R)-3,4-dihydroxy-5-hydroxymethylpiperidine) were synthesised. The isofagomine analogues (3RS,4RS,5RS)N-(2-phosphonoethyl)-3,4-dihydroxy-5-hydroxymethyl-piperidine, (3SR,4SR,5RS)-N-(2-phosphonoethyl)-3,4-dihydroxy-5-hydroxy-methylpiperidine, and (3R,4R,5R)-N-(10-chloro-9-anthracenemethyl)-3,4-dihydroxy-5-hydroxy-methylpiperidine were synthesised by direct alkylation of the corresponding azasugar. N-Substituted noeuromycin derivatives could not be made in this straightforward manner, but were made by modification of a synthesis intermediate. By this method (2RS,3S,4R,5R)-N-(4-methoxyphenyl)-2,3,4-trihydroxy-5-hydroxymethylpiperidine and (2RS,3S,4R,5R)-N-nonyl-2,3,4-trihydroxy-5-hydroxymethylpiperidine were synthesised. The stability of noeuromycin was studied and was found to depend on stereochemistry and pH. The L-fuco isomer ((2RS, 3R,4R,5R)-2,3,4-trihydroxy-5-methylpiperidine) was observed to undergo a particularly facile Amadori rearrangement at neutral pH to the 3-ketopiperidine. A noeuromycin analogue, that could not undergo the Amadori rearrangement, was synthesised.

  DOI：

  10.1081/car-200030070
• 作为产物：
  描述：

  4-甲氧基苄胺 、 4-O-benzyl-2-deoxy-2-C-hydroxymethyl-D-glucopyranose 在 sodium cyanoborohydride 作用下， 以 水 、 甲醇 为溶剂， 反应 21.0h， 生成 (2R,3S,4R,5R)-3-Benzyloxy-5-[(4-methoxy-benzylamino)-methyl]-hexane-1,2,4,6-tetraol
  参考文献：
  名称：

  Synthesis and Chemistry of Noeuromycin and Isofagomine Analogues

  摘要：

  Several N-substituted analogues of noeuromycin ((2RS,3S,4R,5R)-2,3,4-trihydroxy-5 -hydroxymethylpiperidine) and isofagomine ((3R,4R,5R)-3,4-dihydroxy-5-hydroxymethylpiperidine) were synthesised. The isofagomine analogues (3RS,4RS,5RS)N-(2-phosphonoethyl)-3,4-dihydroxy-5-hydroxymethyl-piperidine, (3SR,4SR,5RS)-N-(2-phosphonoethyl)-3,4-dihydroxy-5-hydroxy-methylpiperidine, and (3R,4R,5R)-N-(10-chloro-9-anthracenemethyl)-3,4-dihydroxy-5-hydroxy-methylpiperidine were synthesised by direct alkylation of the corresponding azasugar. N-Substituted noeuromycin derivatives could not be made in this straightforward manner, but were made by modification of a synthesis intermediate. By this method (2RS,3S,4R,5R)-N-(4-methoxyphenyl)-2,3,4-trihydroxy-5-hydroxymethylpiperidine and (2RS,3S,4R,5R)-N-nonyl-2,3,4-trihydroxy-5-hydroxymethylpiperidine were synthesised. The stability of noeuromycin was studied and was found to depend on stereochemistry and pH. The L-fuco isomer ((2RS, 3R,4R,5R)-2,3,4-trihydroxy-5-methylpiperidine) was observed to undergo a particularly facile Amadori rearrangement at neutral pH to the 3-ketopiperidine. A noeuromycin analogue, that could not undergo the Amadori rearrangement, was synthesised.

  DOI：

  10.1081/car-200030070