2,6,7-Trideoxy-2,6-imino-L-glycero-L-gluco-heptitol | 185745-80-6

• 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: 2,6,7-Trideoxy-2,6-imino-L-glycero-L-gluco-heptitol
• 英文别名: epi-Homorhamnojirimycin；(2S,3S,4R,5S,6R)-2-(hydroxymethyl)-6-methylpiperidine-3,4,5-triol；Epihomorhamnojirimycin
• CAS: 185745-80-6
• 化学式: C₇H₁₅NO₄
• 分子量: 177.2
• InChiKey: ZEWFPWKROPWRKE-PFCGLBSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,6,7-Trideoxy-2,6-imino-3,4-O-isopropylidene-D-glycero-L-talo-heptono-1,5-lactone 在 锂硼氢 、 acidic ion exchange resin 作用下， 生成 2,6,7-Trideoxy-2,6-imino-L-glycero-L-gluco-heptitol
  参考文献：
  名称：

  L-鼠李糖的哌啶类似物对柚皮苷酶（L-鼠李糖苷酶）的抑制作用：用于包含三羟基哌酸的文库的支架

  摘要：

  L-Deoxyrhamnojirimycin 1不能显着抑制柚皮苷酶，但是5- epi -L-deoxyrhamnojirimycin 2是有效的抑制剂。相反，α-C-糖苷1是L-鼠李糖苷酶的良好抑制剂，而这些的2则不是。中间的氮杂双环内酯可能用于将许多三羟基哌酸掺入肽文库中。

  DOI：

  10.1016/0040-4039(96)01958-2

文献信息

• The Synthesis of Deoxygalactostatin and 2,6-Imino-heptitol Derivatives via Stannane Mediated Hydroxymethylation of 5-Azido-1,4-lactones
  作者：John P. Shilvock、George W. J. Fleet

  DOI：10.1055/s-1998-1698

  日期：1998.5

  Deoxygalactostatin, homogalactonojirimycin derivatives and other 2,6-imino-heptitols are accessed via the nucleophilic addition of a hydroxymethyl anion equivalent to 5-azido-1,4-lactones to afford 6-azido-lactols. Subsequent hydrogenation induces intramolecular reductive amination to produce the desired piperidine ring systems.

  通过与 5-叠氮-1,4-内酯等效的羟甲基阴离子的亲核加成，可以获得脱氧半乳糖肽、同半乳糖霉素衍生物和其他 2,6-亚氨基庚醇，从而得到 6-叠氮内酯。随后的氢化诱导分子内还原胺化，生成所需的哌啶环系统。
• Piperidine analogues of D-galactose as potent inhibitors of α-galactosidase: Synthesis by stannane-mediated hydroxymethylation of 5-azido-1,4-lactones. Structural relationships between D-galactosidase and L-rhamnosidase inhibitors
  作者：John P. Shilvock、Robert J. Nash、Alison A. Watson、Ana L. Winters、Terry D. Butters、Raymond A. Dwek、David A. Winkler、George W. J. Fleet

  DOI：10.1039/a904145a

  日期：——

  The syntheses of the polyhydroxylated piperidines deoxygalactonojirimycin 2, homogalactonojirimycins 7 and 9, and other 2,6-iminoheptitol derivatives, including an analogue of L-altropyranose, are reported. 5-Azidoaldono-1,4-lactones undergo chain extension to afford azido lactols by the addition of a hydroxymethyllithium species 18, generated by transmetallation of a protected stannylmethanol derivative 17. Hydrogenation results in azide reduction with subsequent intramolecular reductive amination to give piperidine ring systems. The deprotected iminogalactopyranose analogues are potent and selective α-galactosidase inhibitors. Observations on the structural features determining selectivity of inhibition of α-galactosidases over naringinase (L-rhamnosidase) are also reported.

  报告了多羟基哌啶脱氧半乳糖苷尻霉素 2、均半乳糖苷尻霉素 7 和 9 以及其他 2,6-亚氨基庚醇衍生物（包括一种 L-altropyranose类似物）的合成。5-Azidoaldono-1,4-lactones 经历了链延伸，通过添加羟甲基锂 18 得到叠氮内酯，羟甲基锂是由受保护的链烷甲醇衍生物 17 反金属化生成的。氢化反应导致叠氮还原，随后进行分子内还原胺化反应，得到哌啶环系统。去保护的亚氨基半乳糖类似物是强效的选择性δ-半乳糖苷酶抑制剂。报告还观察了决定δ-半乳糖苷酶抑制柚皮苷酶（L-鼠李糖酶）选择性的结构特征。
• TREATMENT OF LYSOSOMAL STORAGE DISORDERS AND OTHER PROTEOSTATIC DISEASES
  申请人：De Moor Olivier

  公开号：US20110237538A1

  公开（公告）日：2011-09-29

  Described are various compounds, in particular iminosugars, and methods for the treatment of proteostatic diseases, in particular lysosomal storage disorders. The compound may be a pharmacoperone of an enzyme selected from: (a) Acid alpha-glucosidase; (b) Acid beta-glucosidase; (c) glucocerebrosidase; (d) alpha-Galactosidase A; (e) Acid beta-galactosidase; (f) beta-Hexosaminidase A; (g) beta-Hexosaminidase B; (h) Acid sphingomyelinase; (i) Galactocerebrosidase; (j) Acid ceramidase; (k) Arylsulfatase A; (l) alpha-L-Iduronidase; (m) Iduronate-2-sulfatase; (n) Heparan N-sulfatase; (o) alpha-N-Acetylglucosaminidase; (p) Acetyl-CoA: alpha-glucosaminide N-acetyltransferase; (q) N-Acetylglucosamine-6-sulfate sulfatase; (r) N-Acetylgalactosamine-6-sulfate sulfatase; (s) Acid beta-galactosidase; (t) Arylsulfatase B; (u) beta-Glucuronidase; (v) Acid alpha-mannosidase; (w) Acid beta-mannosidase; (x) Acid alpha-L-fucosidase; (y) Sialidase; and (z) alpha-N-acetylgalactosaminidase.
• Inhibition of naringinase (L-rhamnosidase) by piperidine analogues of L-rhamnose: Scaffolds for libraries incorporating trihydroxypipecolic acids
  作者：John P. Shilvock、Joseph R. Wheatley、Benjamin Davis、Robert J. Nash、Rhodri C. Griffiths、M.George Jones、Matthias Müller、Sarah Crook、David J. Watkin、Colin Smith、Gurdyal S. Besra、Patrick J. Brennan、George W.J. Fleet

  DOI：10.1016/0040-4039(96)01958-2

  日期：1996.11

  L-Deoxyrhamnojirimycin 1 does not inhibit naringinase significantly but 5-epi-L-deoxyrhamnojirimycin 2 is a potent inhibitor. Conversely, α-C-glycosides of 1 are good inhibitors of L-rhamnosidase whereas those of 2 are not. Intermediate azabicyclic lactones are likely to be of use for the incorporation of a number of trihydroxypipecolic acids into peptide libraries.

  L-Deoxyrhamnojirimycin 1不能显着抑制柚皮苷酶，但是5- epi -L-deoxyrhamnojirimycin 2是有效的抑制剂。相反，α-C-糖苷1是L-鼠李糖苷酶的良好抑制剂，而这些的2则不是。中间的氮杂双环内酯可能用于将许多三羟基哌酸掺入肽文库中。