(-)-N-acetyl-isofagomine | 215725-11-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (-)-N-acetyl-isofagomine
• 英文别名: 1-[(3S,4S,5S)-3,4-Dihydroxy-5-(hydroxymethyl)piperidin-1-yl]ethan-1-one；1-[(3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)piperidin-1-yl]ethanone
• CAS: 215725-11-4
• 化学式: C₈H₁₅NO₄
• 分子量: 189.211
• InChiKey: YOYUKMUNSDJLHM-FXQIFTODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  81
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3S,4S,5S)-N-benzyl-3,4-diacetoxy-5-(acetoxymethyl)piperidine 在 palladium on activated charcoal 吡啶 、 氨 、 氢气 作用下， 以 甲醇 为溶剂， 生成 (-)-N-acetyl-isofagomine
  参考文献：
  名称：

  Synthesis of (−)‐Isofagomine

  摘要：

  1,3-Dipolar cycloaddition of N-benzyl nitrone 2 to delta-lactone 15 proceeded with excellent stereoselectivity to provide only one adduct 16. Cycloadduct 16 was subsequently subjected to a sequence of reactions involving rearrangement to gamma-lactone, glycolic cleavage/reduction, protection of the terminal hydroxymethyl group, reduction of the lactone, desilylation/mesylation, and hydrogenolysis of the N-O bond providing (-)-isofagomine and its N-substituted derivatives. The biologic activity of N-substituted (-)-isofagomines toward commercially available alpha- and beta-glucosidases, alpha-D-mannosidase, alpha-L-fucosidase, beta-D-glucuronidase, and beta-D-galactosidase was tested.

  DOI：

  10.1080/07328300601039336

文献信息

• NOVEL HETEROCYCLIC COMPOUNDS
  申请人：NOVO NORDISK A/S

  公开号：EP0983239A1

  公开（公告）日：2000-03-08
• [EN] NOVEL HETEROCYCLIC COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES HETEROCYCLIQUES
  申请人：NOVO NORDISK A/S

  公开号：WO1998050359A1

  公开（公告）日：1998-11-12

  (EN) Novel piperidine compounds are provided, and those compounds are useful in the treatment and/or prevention of diabetes, and especially non-insulin dependent diabetes (NIDDM or type 2 diabetes) including overnight or meal treatment and treatment or prevention of long-term complications, such as retinopathy, neuropathy, nephropathy, and micro- and macro-angiopathy; treatment of hyperglycemia, hypercholesterolemia, hypertension, hyperinsulinemia, hyperlipidemia, atherosclerosis or myocardial ischemia.(FR) L'invention concerne de nouveaux composés de pipéridine. Ces composés permettent de traiter et/ou de prévenir le diabète, et en particulier, le diabète non insulino-dépendant (NIDDM ou diabète de type 2). Ils sont également utiles dans le traitement de nuit ou au cours des repas, et le traitement ou la prévention de complications à long terme, comme la rétinopathie, la neuropathie, la néphropathie, et la micro- et macro-angiopathie, le traitement de l'hyperglycémie, l'hypercholestérolémie, l'hypertension, l'hyperinsulinémie, l'hyperlipidémie, l'athérosclérose ou l'ischémie myocardique.
• Synthesis of (−)‐Isofagomine
  作者：Irma Panfil、Jolanta Solecka、Marek Chmielewski

  DOI：10.1080/07328300601039336

  日期：2006.12.1

  1,3-Dipolar cycloaddition of N-benzyl nitrone 2 to delta-lactone 15 proceeded with excellent stereoselectivity to provide only one adduct 16. Cycloadduct 16 was subsequently subjected to a sequence of reactions involving rearrangement to gamma-lactone, glycolic cleavage/reduction, protection of the terminal hydroxymethyl group, reduction of the lactone, desilylation/mesylation, and hydrogenolysis of the N-O bond providing (-)-isofagomine and its N-substituted derivatives. The biologic activity of N-substituted (-)-isofagomines toward commercially available alpha- and beta-glucosidases, alpha-D-mannosidase, alpha-L-fucosidase, beta-D-glucuronidase, and beta-D-galactosidase was tested.