N-[(2R,3R,4S)-3,4,6-trihydroxy-1,5-dioxohexan-2-yl]acetamide | 153373-83-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2R,3R,4S)-3,4,6-trihydroxy-1,5-dioxohexan-2-yl]acetamide
• CAS: 153373-83-2
• 化学式: C₈H₁₃NO₆
• 分子量: 219.194
• InChiKey: DQGPHTHBCBFFDM-UIISKDMLSA-N

物化性质

• 沸点：
  636.5±55.0 °C(Predicted)
• 密度：
  1.417±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[(2R,3R,4S)-3,4,6-trihydroxy-1,5-dioxohexan-2-yl]acetamide 在 palladium hydroxide - carbon 盐酸 、 氢气 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 341.0h， 生成 2-乙酰氨基-1,2,5-三脱氧-1,5-亚氨基-d-葡萄糖醇
  参考文献：
  名称：

  2-Acetamido-1,2-dideoxynojirimycin: an improved synthesis

  摘要：

  The potent beta-N-acetylglucosaminidase inhibitor, 2-acetamido-1,2-dideoxynojirimycin, was prepared in 6 steps from N-acetyl-D-glucosamine (overall yield 10%) via the double reductive amination of a keto aldehyde as the key step.

  DOI：

  10.1016/s0040-4020(01)80229-5
• 作为产物：
  描述：

  2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline 在 溴 、 三正丁基甲氧基锡 、 二正丁基氧化锡 、 对甲苯磺酸 作用下， 以 硫酸 、 水 、 溶剂黄146 为溶剂， 反应 14.25h， 生成 N-[(2R,3R,4S)-3,4,6-trihydroxy-1,5-dioxohexan-2-yl]acetamide
  参考文献：
  名称：

  2-Acetamido-1,2-dideoxynojirimycin: an improved synthesis

  摘要：

  The potent beta-N-acetylglucosaminidase inhibitor, 2-acetamido-1,2-dideoxynojirimycin, was prepared in 6 steps from N-acetyl-D-glucosamine (overall yield 10%) via the double reductive amination of a keto aldehyde as the key step.

  DOI：

  10.1016/s0040-4020(01)80229-5

文献信息

• Iminosugar glycoconjugates
  申请人：Technische Universität Graz

  公开号：EP1903034A1

  公开（公告）日：2008-03-26

  The iminosugar conjugates according to the invention are N-alkylated 1,5-dideoxy-1,5-iminohexitol or 1,5-dideoxy-1,5-iminopentitol derivatives. The iminosugar component can be, for example, D-gluco-, L-ido-, D-galacto-, D-manno-, 2-acetamido-2-deoxy-D-gluco- or xylo-configuration. The N-substituent is a protected L-α-aminoacid derivative, showing L-lysine-like structural features. The linkage between the carbohydrate and the peptide component is not via the usual glycosidic position, but shows structural features of a very stable tertiary amine. Thus the linkage is very stable. These new compounds are synthesised by using catalytic intramolecular reductive amination of dicarbonyl sugars with partially protected amino acids. The process of intramolecular reductive amination itself is carried out using Pearlman's catalyst (Pd(OH)2/C) and H2 at ambient pressure and room temperature. The resulting accessible class of iminosugar conjugate compounds is represented by the general structure shown in Figure 4(c). The alkyl chain length parameter n can be freely chosen from n=0 upwards. Preferably n is between 0 and 10, and more preferably n is 2, 3, or 4. Residue R1 can be chosen from H, OH, or NHAc, with Ac being Acetyl. R2 can be H, OH, or NHAc. R3, R4, R5, R6 can be H or OH. R7 and R8 can be H, CH2OH CH3, COQH, or COOR with R being Alkyl or Aryl. R9 and R10 can be chosen from H, NH2, NHR, with R being a protective group, an amino acid, a peptide, or a protein. R11 can be OH, O-Alkyl, O-Aryl, NH2, N-Alkyl, N-Aryl, amino acid or peptide, connected via an amide bond.

  本发明涉及的亚氨基糖缀合物是N-烷基化的1,5-二脱氧-1,5-亚氨基己糖醇或1,5-二脱氧-1,5-亚氨基戊糖醇衍生物。亚氨基糖部分可以是例如D-葡萄糖、L-艾杜糖、D-半乳糖、D-甘露糖、2-乙酰氨基-2-脱氧-D-葡萄糖或木糖构型。N-取代基是一种保护的L-α-氨基酸衍生物，显示出类似L-赖氨酸的结构特征。糖和肽组分之间的连接不是通过常规的糖苷位置，而是显示出非常稳定的叔胺的结构特征。因此，这种连接非常稳定。这些新化合物是通过使用催化剂催化二羰基糖与部分保护的氨基酸之间的分子内还原胺化合成的。分子内还原胺化过程本身是在常压和室温下使用Pearlman催化剂（Pd(OH)2/C）和氢气进行的。由此得到的一类亚氨基糖缀合物化合物的可及性由图4(c)所示的通用结构表示。烷基链长参数n可以从n=0开始自由选择。优选n在0到10之间，更优选n为2、3或4。残基R1可以从H、OH或NHAc中选择，其中Ac代表乙酰基。R2可以是H、OH或NHAc。R3、R4、R5、R6可以是H或OH。R7和R8可以是H、CH2OH、CH3、COQH或COOR，其中R是烷基或芳基。R9和R10可以从H、NH2、NHR中选择，其中R是一个保护基团、氨基酸、肽或蛋白质。R11可以是OH、O-烷基、O-芳基、NH2、N-烷基、N-芳基、氨基酸或肽，通过酰胺键连接。
• [EN] IMINOSUGAR GLYCOCONJUGATES<br/>[FR] GLYCOCONJUGUÉS IMINOSUCRES
  申请人：UNIV GRAZ TECH

  公开号：WO2008034575A1

  公开（公告）日：2008-03-27

  [EN] The iminosugar conjugates having the structural formula (I) with integer n=0; R¹, R², being chosen from H, OH, NHAc, OGlycosyl, O(CH₂)_mCH₃, or O(CF₂)_mCF₃; R³, R⁴, R⁵, and R⁶ being chosen from H, OH, OGlycosyl, O(CH₂)_mCH₃, or O(CF₂)_mCF₃; with integer m between 1 and 10; R⁷ and R^7a being chosen from H, CH₂OH, CH₃, COOH, COO-Alkyl, or COO-Aryl, whereby at least R⁷ or R^7a is chosen to be H; R⁹ and R¹⁰ being chosen from H, NH₂, NHR, with R being a protective group, an amino acid, a peptide, or a protein; and R¹¹ being chosen from OH, O-Alkyl, O-Aryl, NH₂, N-Alkyl, N-Aryl, amino acid or peptide, connected via an amide bond, are claimed.
  [FR] L'invention concerne des conjugués iminosucres ayant la formule structurale (I) avec n entier = 0 ; R¹, R² étant choisis parmi H, OH, NHAc, Oglycosyle, O(CH₂)_mCH₃ ou O(CF₂)_mCF₃ ; R³, R⁴, R⁵ et R⁶ étant choisis parmi H, OH, Oglycosyle, O(CH₂)_mCH₃ ou O(CF₂)_mCF₃ ; avec m entier entre 1 et 10 ; R⁷ et R^7a étant choisis parmi H, CH₂OH, CH₃, COOH, COO-alkyle ou COO-aryle, ce par quoi au moins R⁷ ou R^7a est choisi pour être H ; R⁹ et R¹⁰ étant choisis parmi H, NH₂, NHR, R étant un groupe protecteur, un acide aminé, un peptide ou une protéine ; et R¹¹ étant choisi parmi OH, O-alkyle, O-aryle, NH₂, N-alkyle, N-aryle, acide aminé ou peptide, lié par l'intermédiaire d'une liaison amide.
• 2-Acetamido-1,2-dideoxynojirimycin: an improved synthesis
  作者：Richard H. Furneaux、Graeme J. Gainsford、Gregory P. Lynch、Selwyn C. Yorke

  DOI：10.1016/s0040-4020(01)80229-5

  日期：——

  The potent beta-N-acetylglucosaminidase inhibitor, 2-acetamido-1,2-dideoxynojirimycin, was prepared in 6 steps from N-acetyl-D-glucosamine (overall yield 10%) via the double reductive amination of a keto aldehyde as the key step.