5-epi-Deoxyrhamnojirimycin | 135395-58-3

• 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: 5-epi-Deoxyrhamnojirimycin
• 英文别名: (2R,3S,4S,5S)-2-methylpiperidine-3,4,5-triol
• CAS: 135395-58-3
• 化学式: C₆H₁₃NO₃
• 分子量: 147.174
• InChiKey: VYOCYWDJTQRZLC-VANKVMQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-deoxy-2,3-O-isopropylidene-L-talono-1,4-lactone 在 盐酸 、 palladium on activated charcoal 、 sodium azide 、 dimethyl sulfide borane 、 水 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-epi-Deoxyrhamnojirimycin
  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

• Synthesis of 1,6-Dideoxynojirimycin, 1,6-Dideoxy-D-allo-nojirimycin, and 1,6-Dideoxy-D-gulo-nojirimycinvia Asymmetric Hetero-Diels-Alder Reactions
  作者：Albert Defoin、Herv� Sarazin、Jacques Streith

  DOI：10.1002/hlca.19960790223

  日期：1996.3.20

  Asymmetric Diels-Alder reaction of sorbaldehyde O-methyloxime 1d with chiral chloronitroso derivative 2 of D-mannose, followed by osmylation of the primary cycloadduct, led to diol 6a with excellent enantioselectivity (ee > 99%; Scheme 1). Catalytic hydrogenolysis of 6a gave 1,6-dideoxy-D-allo-nojirimycin (7a). Nucleophilic ring opening of cyclic sulfate 8 allowed a straightforward synthesis of 1,

  不对称狄尔斯-阿尔德反应而山梨醛ö甲基肟1D与手性chloronitroso衍生物2 d甘露糖，接着由主环加成的锇酸酯化，导致二醇6A具有优异的对映选择性（ee值> 99％;方案1）。的催化氢解6A得到1,6-二脱氧D-同种异体-nojirimycin（图7a）。环状硫酸盐8的亲核开环允许直接合成1,6-二脱氧野oji霉素（11）和1,6-二脱氧-D-古洛基-野oji霉素（12；方案2）。
• 6-Deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and d-series, d-fuco-nojirimycin and their 1-deoxyderivatives via hetero-Diels-Alder cycloadditions
  作者：Albert Defoin、Hervé Sarazin、Jacques Streith

  DOI：10.1016/s0040-4020(97)00898-3

  日期：1997.10

  Nucleophilic ring opening of the cyclic sulfates (+/-)-9c and D-9c and of the epoxide (+/-)-13, or double substitution of the bis-triflate D-10 (derived from the Diels-Alder adduct of hexadienal dimethylacetal to achiral or enantiomerically pure nitroso-derivatives) led to 6-deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and D-series, to D-fuco-nojirimycin and to their 1-deoxyderivatives via their crystalline 1-deoxy-1-sulfonic acid derivatives (sulfite adducts). 6-Deoxy-nojirimycin and its isomers are mixtures of alpha- and beta-anomers and of the corresponding imine. (C) 1997 Elsevier Science Ltd.
• 5-epi-Deoxyrhamnojirimycin is a potent inhibitor of an α-l-rhamnosidase: 5-epi-deoxymannojirimycin is not a potent inhibitor of an α-d-mannosidase
  作者：Benjamin G. Davis、Andrew Hull、Colin Smith、Robert J. Nash、Alison A. Watson、David A. Winkler、Rhodri C. Griffiths、George W.J. Fleet

  DOI：10.1016/s0957-4166(98)00317-6

  日期：1998.8

  Whereas deoxyrhamnojirimycin (LRJ) 1 shows no significant inhibition of naringinase (an alpha-L-rhamnosidase), its C-5 epimer 2 is a potent and specific inhibitor of the enzyme and demonstrates the value of unambiguous chemical synthesis of such materials in the evaluation of their biological properties. In contrast, moderately weak inhibition towards an alpha-D-mannosidase is shown by both deoxymannojirimycin (DMJ) 5 and its C-5 epimer 6. Mimics of L-rhamnose which are recognised by enzymes that synthesise or process L-rhamnose may inhibit el ther the biosynthesis of the sugar or its incorporation into mycobacterial cell walls, providing new strategies for the treatment of diseases such as tuberculosis and leprosy. Molecular modelling studies provide a rationale for the surprisingly potent activity of the C-S epimer 2 compared with LRJ 1 and support a general hypothesis that potent piperidine glycosidase inhibitors mimic the H-4(3) conformation Of the relevant glycopyranosyl cation intermediate. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Kajimoto, Tetsuya; Chen, Lihren; Liu, Kevin K.-C., Journal of the American Chemical Society, 1991, vol. 113, # 18, p. 6678 - 6680
  作者：Kajimoto, Tetsuya、Chen, Lihren、Liu, Kevin K.-C.、Wong, Chi-Huey

  DOI：——

  日期：——
• KAJIMOTO, TETSUYA;CHEN, LIHREN;LIU, KEVIN K. -C.;WONG, CHI-HUEY, J. AMER. CHEM. SOC., 113,(1991) N7, C. 6678-6680
  作者：KAJIMOTO, TETSUYA、CHEN, LIHREN、LIU, KEVIN K. -C.、WONG, CHI-HUEY

  DOI：——

  日期：——