tert-butyl (2S,3S,4S,5S)-3,4,5-triacetyloxy-2-(acetyloxymethyl)piperidine-1-carboxylate | 792950-95-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (2S,3S,4S,5S)-3,4,5-triacetyloxy-2-(acetyloxymethyl)piperidine-1-carboxylate
• CAS: 792950-95-9
• 化学式: C₁₉H₂₉NO₁₀
• 分子量: 431.44
• InChiKey: WHZNKOJSBIDPHH-QAETUUGQSA-N

物化性质

• 沸点：
  463.8±38.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3S,4S,5S)-3,4,5-triacetyloxy-2-(acetyloxymethyl)piperidine-1-carboxylate 在 盐酸 、 Dowex 50W-X₈ (H⁺ form) 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以94%的产率得到(2S,3S,4S,5S)-2-(羟甲基)哌啶-3,4,5-三醇
  参考文献：
  名称：

  Biological Properties of d- and l-1-Deoxyazasugars

  摘要：

  L-Enantiomers of 1-deoxynojirimycin (DNJ), 1-deoxymannojirimycin (manno-DNJ), 1-deoxyallonojirimycin (allo-DNJ), 1-deoxyaltronojirimycin (altro-DNJ), 1-deoxygalactonojirimycin (galacto-DNJ), 1-deoxygulonojirimycin (gulo-DNJ), and 1-deoxyldonojirimycin (ido-DNJ) were prepared according to prior methods for the D-enantiomers. These enantiospecific syntheses established unambiguously the absolute configuration of naturally occurring DNJ, manno-DNJ, allo-DNJ, altro-DNJ, and gulo-DNJ. Although D-DNJ and D-galacto-DNJ are known to be powerful competitive inhibitors of alpha-glucosidase and alpha-galactosidase, respectively, with K-i values in the nM range, L-DNJ and L-galacto-DNJ were noncompetitive inhibitors of alpha-glucosidase and alpha-galactosidase, respectively, with K-i values in the PM range. However, the azasugar mimicking the structure of the terminal sugar moiety of the natural substrate is not always an inhibitor of the glycosidase responsible for the hydrolysis. D-manno-DNJ is known as a much better inhibitor of alpha-L-fucosidase than a-mannosidase, while L-allo-DNJ was a better inhibitor than D-manno-DNJ of alpha-mannosidase. L-galacto-DNJ can be regarded as the 6-hydroxylated derivative of deoxyfuconojirimycin (DFJ), which is a powerful inhibitor of alpha-L-fucosidase with a K-i value in the nM range. However, this replacement of the methyl group in DFJ by a hydroxymethyl group reduced its affinity by about 50-fold. This suggests that there is a hydrophobic region in or around the active site of alpha-L-fucosidase. It has been found that inhibitors of human lysosomal glycosidases have therapeutic potential for the corresponding lysosomal storage diseases (Nat. Med. 1999, 5, 112; Proc. Natl. Acad. Sci. USA, 2002, 99, 15428). Inhibition of human lysosomal glycosidases by the 1-deoxyazasugars synthesized was investigated. D-galacto-DNJ is a potent inhibitor of lysosomal alpha-galactosidase (IC50 = 90 nM) and is now being evaluated preclinically for its potential use in Fabry disease, while D-DNJ inhibiting alpha-glucosidase (IC50 = 40 nM) potently does not appear to become a potential therapeutic agent because of additional inhibitory activity toward glycoprotein processing alpha-glucosidases. On the other hand, although L-allo-DNJ is a moderate inhibitor of alpha-mannosidase (IC50 = 64 mu M), it may become a key compound for the drug design of potential therapeutic agents for alpha-mannosidosis.

  DOI：

  10.1021/jm0495881
• 作为产物：
  描述：

  3-反-溴碳-2,2'-二甲基氧酸酯 在 镍 吡啶 、 四氧化锇 、 正丁基锂 、 氢气 、 溶剂黄146 、 N-甲基吗啉氧化物 、 对甲苯磺酰氯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 20.0h， 生成 tert-butyl (2S,3S,4S,5S)-3,4,5-triacetyloxy-2-(acetyloxymethyl)piperidine-1-carboxylate
  参考文献：
  名称：

  A General Approach to the Synthesis of 1-Deoxy-l-iminosugars

  摘要：

  A stereoselective procedure for the preparation of non-naturally occurring deoxy iminosugars belonging to L-series has been developed. The synthesis involves the construction of the key intermediate bicycle pyperidine 8, available in few steps by the coupling of the heterocyclic synthon 3 and the readily available Garner aldehyde 4.

  DOI：

  10.1021/ol7014847