2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-D-glycero-D-ido-heptono-1,4-lactone | 191352-58-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-D-glycero-D-ido-heptono-1,4-lactone
• 英文别名: (4R,4aR,7S,7aS)-7-azido-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4,4a,7,7a-tetrahydrofuro[3,2-d][1,3]dioxin-6-one
• CAS: 191352-58-6
• 化学式: C₁₃H₁₉N₃O₆
• 分子量: 313.31
• InChiKey: ODYWCZQNAUQMCK-KGDYZURWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  77.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-D-glycero-D-ido-heptono-1,4-lactone 在 钯 吡啶 、 咪唑 、 camphor-10-sulfonic acid 、 水 、 氢气 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 [(R)-[(2R,3S,4S)-4-amino-5-oxo-3-triethylsilyloxyoxolan-2-yl]-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl] trifluoromethanesulfonate
  参考文献：
  名称：

  Inhibition of UDP-Gal Mutase and Mycobacterial Galactan Biosynthesis by Pyrrolidine Analogues of Galactofuranose

  摘要：

  Some pyrrolidine analogues of galactofuranose - synthesised from carbohydrate lactones - are the first known inhibitors of E. coli K12 UDP-Gal mutase and mycobacterial galactan biosynthesis.:This inhibition may form a new chemotherapeutic strategy for the treatment of human pathogens which contain integral galactofuranosyl structures such as tuberculosis and leprosy. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01539-6
• 作为产物：
  描述：

  [(4R,4aS,7R,7aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-oxo-4,4a,7,7a-tetrahydrofuro[3,2-d][1,3]dioxin-7-yl] trifluoromethanesulfonate 在 sodium azide 作用下， 生成 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-D-glycero-D-ido-heptono-1,4-lactone
  参考文献：
  名称：

  Glucopyranose Spirohydantoins: Specific Inhibitors of Glycogen Phosphorylase

  摘要：

  本文描述了利用一种现成的庚内酯简短合成葡萄糖吡喃糖 1δ²（一种有效的糖原磷酸化酶特异性抑制剂）的螺海因及其非活性同分异构体 1δ±的过程；这是首次合成吡喃糖的螺海因，其中吡喃糖环是在海因环之后形成的。

  DOI：

  10.1055/s-1997-940277

文献信息

• An approach to 8 stereoisomers of homonojirimycin from d-glucose via kinetic & thermodynamic azido-γ-lactones
  作者：Andreas F. G. Glawar、Sarah F. Jenkinson、Scott J. Newberry、Amber L. Thompson、Shinpei Nakagawa、Akihide Yoshihara、Kazuya Akimitsu、Ken Izumori、Terry D. Butters、Atsushi Kato、George W. J. Fleet

  DOI：10.1039/c3ob41334a

  日期：——

  Crystal structures were obtained for the two C2 epimeric azido-γ-lactones 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-D-glycero-D-ido-heptono-1,4-lactone and 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-D-glycero-D-gulo-heptono-1,4-lactone prepared from kinetic and thermodynamic azide displacements of a triflate derived from D-glucoheptonolactone. Azido-γ-lactones are very useful intermediates in the synthesis of iminosugars and polyhydroxylated amino acids. In this study two epimeric azido-heptitols allow biotechnological transformations via Izumoring techniques to 8 of the 16 possible homonojirimycin analogues, 5 of which were isolated pure because of the lack of stereoselectivity of the final reductive amination. A side-by-side glycosidase inhibition profile of 11 of the possible 16 HNJ stereoisomers derived from D-glucose and D-mannose is presented.

  获得两种 C2 差向叠氮-γ-内酯 2-叠氮-2-脱氧-3,5:6,7-二-O-异丙叉-D-甘油-D-ido-庚酮-1,4- 的晶体结构内酯和 2-叠氮基-2-脱氧-3,5:6,7-二-O-异亚丙基-D-甘油-D-古洛-庚酮-1,4-内酯由三氟甲磺酸酯的动力学和热力学叠氮化物置换制备来自D-葡萄糖庚酸内酯。叠氮基-γ-内酯是亚氨基糖和多羟基氨基酸合成中非常有用的中间体。在这项研究中，两种差向异构叠氮庚醇允许通过 Izumoring 技术对 16 种可能的高野尻霉素类似物中的 8 种进行生物技术转化，其中 5 种由于最终还原胺化缺乏立体选择性而被分离纯化。提出了衍生自 D-葡萄糖和 D-甘露糖的 16 种可能的 HNJ 立体异构体中的 11 种的并列糖苷酶抑制谱。
• Inhibition of UDP-Gal Mutase and Mycobacterial Galactan Biosynthesis by Pyrrolidine Analogues of Galactofuranose
  作者：Richard E Lee、Martin D. Smith、Robert J. Nash、Rhodri C. Griffiths、Michael McNeil、Ravinder K. Grewal、Wenxin Yan、Gurdyal S. Besra、Patrick J. Brennan、George W.J. Fleet

  DOI：10.1016/s0040-4039(97)01539-6

  日期：1997.9

  Some pyrrolidine analogues of galactofuranose - synthesised from carbohydrate lactones - are the first known inhibitors of E. coli K12 UDP-Gal mutase and mycobacterial galactan biosynthesis.:This inhibition may form a new chemotherapeutic strategy for the treatment of human pathogens which contain integral galactofuranosyl structures such as tuberculosis and leprosy. (C) 1997 Elsevier Science Ltd.
• Glucopyranose Spirohydantoins: Specific Inhibitors of Glycogen Phosphorylase
  作者：Carmen de la Fuente、Thomas Krülle、Kimberley Watson、Mary Gregoriou、Louise Johnson、Katerina Tsitsanou、Spyros Zographos、Nikos Oikonomakos、George Fleet

  DOI：10.1055/s-1997-940277

  日期：1997.6

  A short synthesis of the spirohydantoin of glucopyranose 1β [a potent and specific inhibitor of glycogen phosphorylase], together with its inactive anomer 1α, from a readily available heptonolactone is described; this is the first synthesis of a spirohydantoin of a pyranose in which the pyranose ring is formed after the hydantoin ring.

  本文描述了利用一种现成的庚内酯简短合成葡萄糖吡喃糖 1δ²（一种有效的糖原磷酸化酶特异性抑制剂）的螺海因及其非活性同分异构体 1δ±的过程；这是首次合成吡喃糖的螺海因，其中吡喃糖环是在海因环之后形成的。