(2S,3S,4R,5R,6R)-tert-butyl 2-allyl-3,4,5-tris(benzyloxy)-6-hydroxyazepane-1-carboxylate | 1354826-76-8

• 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: (2S,3S,4R,5R,6R)-tert-butyl 2-allyl-3,4,5-tris(benzyloxy)-6-hydroxyazepane-1-carboxylate
• 英文别名: tert-butyl (2S,3S,4R,5R,6R)-6-hydroxy-3,4,5-tris(phenylmethoxy)-2-prop-2-enylazepane-1-carboxylate
• CAS: 1354826-76-8
• 化学式: C₃₅H₄₃NO₆
• 分子量: 573.73
• InChiKey: YNSSJHVKFNGFMR-RGPGAZMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R,6R)-tert-butyl 2-allyl-3,4,5-tris(benzyloxy)-6-hydroxyazepane-1-carboxylate 在 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 8.0h， 生成 (2S,3S,4R,5R,6S)-tert-butyl 2-allyl-3,4,5-tris(benzyloxy)-6-hydroxyazepane-1-carboxylate
  参考文献：
  名称：

  Access to l- and d-Iminosugar C-Glycosides from a d-gluco-Derived 6-Azidolactol Exploiting a Ring Isomerization/Alkylation Strategy

  摘要：

  A flexible synthetic access to six-membered and D-iminosugar C-glycosides is reported starting from the easily available 6-azido-6-deoxy-2,3,4-tri-O-benzyl-D-glucopyranose precursor. This methodology involves a highly diastereoselective tandem ring enlargement/alkylation and a stereocontrolled ring contraction. It allows an efficient synthesis of iminosugar C-glycosides displaying structural diversity at both C-1 and C-6.

  DOI：

  10.1021/ol203385w
• 作为产物：
  描述：

  6-azido-6-deoxy-2,3,4-tri-O-benzyl-D-glucopyranose 在 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 (2S,3S,4R,5R,6R)-tert-butyl 2-allyl-3,4,5-tris(benzyloxy)-6-hydroxyazepane-1-carboxylate
  参考文献：
  名称：

  Access to l- and d-Iminosugar C-Glycosides from a d-gluco-Derived 6-Azidolactol Exploiting a Ring Isomerization/Alkylation Strategy

  摘要：

  A flexible synthetic access to six-membered and D-iminosugar C-glycosides is reported starting from the easily available 6-azido-6-deoxy-2,3,4-tri-O-benzyl-D-glucopyranose precursor. This methodology involves a highly diastereoselective tandem ring enlargement/alkylation and a stereocontrolled ring contraction. It allows an efficient synthesis of iminosugar C-glycosides displaying structural diversity at both C-1 and C-6.

  DOI：

  10.1021/ol203385w

文献信息

• N- and C-alkylation of seven-membered iminosugars generates potent glucocerebrosidase inhibitors and F508del-CFTR correctors
  作者：J. Désiré、M. Mondon、N. Fontelle、S. Nakagawa、Y. Hirokami、I. Adachi、R. Iwaki、G. W. J. Fleet、D. S. Alonzi、G. Twigg、T. D. Butters、J. Bertrand、V. Cendret、F. Becq、C. Norez、J. Marrot、A. Kato、Y. Blériot

  DOI：10.1039/c4ob00325j

  日期：——

  carbon atom alkyl chains have been introduced. The study of two distinct D-gluco and L-ido stereochemistries for the tetrol pattern as well as R and S configurations for the C-2 carbon bearing the C-alkyl chain is reported. We observed that C-alkylation of the L-ido tetrahydroxylated azepane converts it from an α-L-fucosidase to a β-glucosidase and β-galactosidase inhibitor while N-alkylation of the

  已经广泛研究了合成的C-烷基和N-烷基六元亚氨基糖的糖苷酶抑制特性，从而产生了治疗候选物。尽管报道了有前途的结构，但相关的七元亚氨基环醇却很少被检查。使用室内环扩大/ C-烷基化以及交叉复分解方法学作为关键步骤，我们从易于获得的起始位置开始进行了14个2 C-和8个N-烷基四羟基化氮杂环丙烷的文库的合成和生物学评估。吡喃葡萄糖衍生的叠氮吲哚。已经引入了四个，六个，九个和十二个碳原子烷基链。两个不同的研究d -葡萄糖和大号- IDO为四醇图案以及立体化学ř和小号的C-2碳承载的配置Ç报道烷基链。我们观察到的该C-烷基化大号- IDO四羟基从α-氮杂环庚烷将其转换大号-fucosidase到β葡糖苷酶和β半乳糖苷酶抑制剂，而N-烷基化d -葡糖亚氨基糖显著提高了其抑制轮廓导致有力的无论烷基链的立体化学如何，β-葡萄糖苷酶，β-半乳糖苷酶，α- L-鼠李糖苷酶和β-葡萄糖醛酸苷酶抑制剂。有趣的是
• Structural variation of the 3-acetamido-4,5,6-trihydroxyazepane iminosugar through epimerization and <i>C</i>-alkylation leads to low micromolar HexAB and NagZ inhibitors
  作者：J. Bouquet、N. Auberger、R. Ashmus、D. King、A. Bordes、N. Fontelle、S. Nakagawa、Z. Madden、C. Proceviat、A. Kato、J. Désiré、D. J. Vocadlo、Y. Blériot

  DOI：10.1039/d1ob02280f

  日期：——

  Escherichia coli NagZ. Capitalizing on the flexibility of azepanes and the active site tolerances of hexosaminidases, we explore the effects of epimerization of stereocenters at C-3, C-5 and C-6 and C-alkylation at the C-2 or C-7 positions. Accordingly, epimerization at C-6 (L-ido) and at C-5 (D-galacto) led to selective HexAB inhibitors whereas introduction of a propyl group at C-7 on the C-3 epimer furnished

  我们报告了衍生自 3 S -acetamido-4 R ,5 R ,6 S -trihydroxyazepane 支架的七元亚氨基糖的合成及其作为功能相关外-N -乙酰氨基己糖苷酶抑制剂的评估，包括人O -GlcNAcase (OGA)，人溶酶体 β-氨基己糖苷酶 (HexAB) 和大肠杆菌NagZ。利用氮杂环丁烷的灵活性和氨基己糖苷酶的活性位点耐受性，我们探讨了立体中心在 C-3、C-5 和 C-6 的差向异构化以及C-2 或 C-7 位置的C-烷基化的影响。因此，在 C-6 ( L -ido) 和 C-5 ( D-galacto) 导致选择性 HexAB 抑制剂，而在 C-3 差向异构体的 C-7 处引入丙基提供有效的 NagZ 抑制剂。
• Access to <scp>l</scp>- and <scp>d</scp>-Iminosugar C-Glycosides from a <scp>d</scp>-<i>gluco</i>-Derived 6-Azidolactol Exploiting a Ring Isomerization/Alkylation Strategy
  作者：Martine Mondon、Nathalie Fontelle、Jérôme Désiré、Frédéric Lecornué、Jérôme Guillard、Jérôme Marrot、Yves Blériot

  DOI：10.1021/ol203385w

  日期：2012.2.3

  A flexible synthetic access to six-membered and D-iminosugar C-glycosides is reported starting from the easily available 6-azido-6-deoxy-2,3,4-tri-O-benzyl-D-glucopyranose precursor. This methodology involves a highly diastereoselective tandem ring enlargement/alkylation and a stereocontrolled ring contraction. It allows an efficient synthesis of iminosugar C-glycosides displaying structural diversity at both C-1 and C-6.