(2R',3R',4R')-1-N-(benzyloxycarbonyl)-2-acetamido-3-hydroxy-4-(tert-butyldimethylsilyloxy)-piperidine | 865996-22-1

• 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: (2R',3R',4R')-1-N-(benzyloxycarbonyl)-2-acetamido-3-hydroxy-4-(tert-butyldimethylsilyloxy)-piperidine
• 英文别名: (2S,3R,4R)-2-acetamido-1-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxypiperidine；benzyl (2S,3R,4R)-2-acetamido-4-[tert-butyl(dimethyl)silyl]oxy-3-hydroxypiperidine-1-carboxylate
• CAS: 865996-22-1
• 化学式: C₂₁H₃₄N₂O₅Si
• 分子量: 422.597
• InChiKey: HUHOCMLLQUDAMW-QYZOEREBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R',3R',4R')-1-N-(benzyloxycarbonyl)-2-acetamido-3-hydroxy-4-(tert-butyldimethylsilyloxy)-piperidine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以98%的产率得到2-acetamido-4-(tert-butyldimethylsilyloxy)-3-hydroxypiperidine
  参考文献：
  名称：

  Synthesis and Kinetic Analysis of the N-Acetylhexosaminidase Inhibitor XylNAc-Isofagomine

  摘要：

  An efficient 10-step preparation from 4-methoxypyridine of (2R,3R,4R)-2-acetamido-3,4-dihydroxypiperidine ("XyINAe-isofagomine") in optically active form is described. Key steps include an enantioselective reduction with catecholborane/(S)-2-methyl-CBS-oxazaborolidine, and a stereo-selective pseudo-glycosylation of lithium azide by a cyclic sulfite ester. The title compound showed a K-i = 21 mu M when evaluated against the N-acetyl-beta-hexosaminidase from Streptomyces plicatus.

  DOI：

  10.1021/jo051117e
• 作为产物：
  描述：

  4-甲氧基吡啶 在 咪唑 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 四氧化锇 、 氯化亚砜 、 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 、 镍 、 N-甲基吗啉氧化物 、 (S)-2-甲基-CBS-恶唑硼烷 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 58.0h， 生成 (2R',3R',4R')-1-N-(benzyloxycarbonyl)-2-acetamido-3-hydroxy-4-(tert-butyldimethylsilyloxy)-piperidine
  参考文献：
  名称：

  Synthesis and Kinetic Analysis of the N-Acetylhexosaminidase Inhibitor XylNAc-Isofagomine

  摘要：

  An efficient 10-step preparation from 4-methoxypyridine of (2R,3R,4R)-2-acetamido-3,4-dihydroxypiperidine ("XyINAe-isofagomine") in optically active form is described. Key steps include an enantioselective reduction with catecholborane/(S)-2-methyl-CBS-oxazaborolidine, and a stereo-selective pseudo-glycosylation of lithium azide by a cyclic sulfite ester. The title compound showed a K-i = 21 mu M when evaluated against the N-acetyl-beta-hexosaminidase from Streptomyces plicatus.

  DOI：

  10.1021/jo051117e

文献信息

• New Reactions of Selenocarboxylates
  作者：Spencer Knapp、Etzer Darout

  DOI：10.1021/ol047889z

  日期：2005.1.1

  By treatment with Woollins' reagent in toluene solution, carboxylic acids are converted to selenocarboxylic acids. The latter react in situ to provide new products of acid- or base-promoted substitution, addition, and amidation.
• Synthesis and Kinetic Analysis of the <i>N</i>-Acetylhexosaminidase Inhibitor XylNAc-Isofagomine
  作者：Spencer Knapp、Chunhua Yang、Srihari Pabbaraja、Brian Rempel、Steven Reid、Stephen G. Withers

  DOI：10.1021/jo051117e

  日期：2005.9.1

  An efficient 10-step preparation from 4-methoxypyridine of (2R,3R,4R)-2-acetamido-3,4-dihydroxypiperidine ("XyINAe-isofagomine") in optically active form is described. Key steps include an enantioselective reduction with catecholborane/(S)-2-methyl-CBS-oxazaborolidine, and a stereo-selective pseudo-glycosylation of lithium azide by a cyclic sulfite ester. The title compound showed a K-i = 21 mu M when evaluated against the N-acetyl-beta-hexosaminidase from Streptomyces plicatus.