5-O-benzhydryl-2,3-O-isopropylidene-D-lyxono-1,4-lactone | 1442089-72-6

• 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: 5-O-benzhydryl-2,3-O-isopropylidene-D-lyxono-1,4-lactone
• 英文别名: (3aS,6R,6aS)-6-(benzhydryloxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• CAS: 1442089-72-6
• 化学式: C₂₁H₂₂O₅
• 分子量: 354.403
• InChiKey: SLFINOSQAFJTFF-NEWSRXKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-O-benzhydryl-2,3-O-isopropylidene-D-lyxono-1,4-lactone 在 吡啶 、 咪唑 、 盐酸 、 sodium tetrahydroborate 、 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 碘 、 sodium acetate 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 三乙胺 、 乙酰氯 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 、 叔丁醇 为溶剂， 反应 130.5h， 生成 1,4-dideoxy-2-C-hydroxymethyl-1,4-imino-L-arabinitol
  参考文献：
  名称：

  C-Branched Iminosugars: α-Glucosidase Inhibition by Enantiomers of isoDMDP, isoDGDP, and isoDAB–l-isoDMDP Compared to Miglitol and Miglustat

  摘要：

  The Ho crossed aldol condensation provides access to a series of carbon branched iminosugars as exemplified by the synthesis of enantiomeric pairs of isoDMDP, isoDGDP, and isoDAB, allowing comparison of their biological activities with three linear isomeric natural products DMDP, DGDP, and DAB and their enantiomers. L-IsoDMDP [(2S,3S,4R)-2,4-bis(hydroxymethyl)pyrrolidine-3,4-diol], prepared in 11 steps in an overall yield of 4596 from D-lyxonolactone, is a potent specific competitive inhibitor of gut disaccharidases [K-i 0.081 mu M for rat intestinal maltase] and is more effective in the suppression of hyperglycaemia in a maltose loading test than miglitol, a drug presently used in the treatment of late onset diabetes. The partial rescue of the defective F508del-CFTR function in CF-KM4 cells by L-isoDMDP is compared with miglustat and isoLAB in an approach to the treatment of cystic fibrosis.

  DOI：

  10.1021/jo4005487
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-来苏糖酸-1,4-内酯 、 二苯基重氮甲烷 以 甲苯 为溶剂， 反应 1.0h， 以92%的产率得到5-O-benzhydryl-2,3-O-isopropylidene-D-lyxono-1,4-lactone
  参考文献：
  名称：

  C-Branched Iminosugars: α-Glucosidase Inhibition by Enantiomers of isoDMDP, isoDGDP, and isoDAB–l-isoDMDP Compared to Miglitol and Miglustat

  摘要：

  The Ho crossed aldol condensation provides access to a series of carbon branched iminosugars as exemplified by the synthesis of enantiomeric pairs of isoDMDP, isoDGDP, and isoDAB, allowing comparison of their biological activities with three linear isomeric natural products DMDP, DGDP, and DAB and their enantiomers. L-IsoDMDP [(2S,3S,4R)-2,4-bis(hydroxymethyl)pyrrolidine-3,4-diol], prepared in 11 steps in an overall yield of 4596 from D-lyxonolactone, is a potent specific competitive inhibitor of gut disaccharidases [K-i 0.081 mu M for rat intestinal maltase] and is more effective in the suppression of hyperglycaemia in a maltose loading test than miglitol, a drug presently used in the treatment of late onset diabetes. The partial rescue of the defective F508del-CFTR function in CF-KM4 cells by L-isoDMDP is compared with miglustat and isoLAB in an approach to the treatment of cystic fibrosis.

  DOI：

  10.1021/jo4005487