benzyl 2-C-methyl-β-D-arabinopyranoside | 791067-11-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-C-methyl-β-D-arabinopyranoside
• CAS: 791067-11-3
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: IZXKTBOHRXDTTD-LPWJVIDDSA-N

反应信息

• 作为反应物：
  描述：

  benzyl 2-C-methyl-β-D-arabinopyranoside 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 3 A molecular sieve 、 氢气 、 溴 、 sodium methylate 、 二正丁基氧化锡 、 三乙胺 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 43.58h， 生成 (2R,3S,4R,5R)-5-(hydroxymethyl)-3-methyl-2,3,4-trihydroxy-piperidine
  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：

  benzyl 3,4-O-isopropylidene-2-C-methyl-β-D-arabinopyranoside 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 0.17h， 以98%的产率得到benzyl 2-C-methyl-β-D-arabinopyranoside
  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