1,5,6-trideoxy-1,5-imino-D-galactitol | 135395-47-0

• 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: 1,5,6-trideoxy-1,5-imino-D-galactitol
• 英文别名: 1,5-imino-1,5,6-trideoxy-D-galactitol；1,6-dideoxy-D-galactostatin；1,6-dideoxy-D-galactonojirimycin；(2R,3S,4R,5S)-2-methylpiperidine-3,4,5-triol；D-1,6-dideoxy-galactojirimycin
• CAS: 135395-47-0
• 化学式: C₆H₁₃NO₃
• 分子量: 147.174
• InChiKey: VYOCYWDJTQRZLC-DPYQTVNSSA-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：

  (3aR,6S,6aR)-6-(azidomethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one 在 钯 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 28.0h， 生成 1,5,6-trideoxy-1,5-imino-D-galactitol
  参考文献：
  名称：

  Looking glass inhibitors: efficient synthesis and biological evaluation of d-deoxyfuconojirimycin

  摘要：

  1, 6-Dideoxygalactostatin, the mirror image of 1-deoxy-L-fuconojirimycin, was efficiently prepared from 2,3-Ow-isopropylidene-L-lyxonolactone in four steps and evaluated as a glycosidase inhibitor. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.10.002

文献信息

• A general approach to the synthesis of dideoxy and trideoxyiminoalditols from β-d-glycosides
  作者：Gabriela Pistia、Rawle I. Hollingsworth

  DOI：10.1016/s0008-6215(00)00124-5

  日期：2000.10

  Imino sugars (also called azasugars), a class of compounds of which the 1,5-dideoxy and 1,5,6-trideoxyiminoalditols are members, are important glycosidase inhibitors with very high potential as drugs. Their potential therapeutic applications range from the treatment of diabetes to cancer and AIDS. We present here a general method for the preparation of such compounds with the D-gluco and D-galacto

  氨基糖（也称为氮杂糖）是一类重要的糖苷酶抑制剂，具有作为药物的巨大潜力，其中一类化合物的1，5-二甲氧基和1，5，6-三甲氧基亚氨基醛糖醇是其中的一员。它们的潜在治疗应用范围从糖尿病到癌症和艾滋病。我们在这里提出了一种从β-D-糖苷开始制备具有D-葡萄糖和D-半乳糖构型的化合物的一般方法。该方法特别具有吸引力，因为它具有很高的立体选择性和直接性。关键步骤是将糖苷选择性氧化为己磺酸，并将肟衍生物还原为内酰胺，然后将其进一步还原为目标化合物。如果C-6位带有乙酰氧基，则可以在还原过程中将其脱氧。然后产生三脱氧亚氨基糖。肟还原前的脱乙酰基产生双脱氧化合物。
• ANTIVIRAL PHOSPHONATE ANALOGS
  申请人：Boojamra Constantine G.

  公开号：US20090275535A1

  公开（公告）日：2009-11-05

  The invention is related to phosphorus substituted compounds with antiviral activity, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  这项发明涉及具有抗病毒活性的磷取代化合物，包含这种化合物的组合物以及包括给予这种化合物的治疗方法，还包括用于制备这种化合物的过程和中间体。
• Liposome treatment of viral infections
  申请人：University of Oxford

  公开号：EP2356990A2

  公开（公告）日：2011-08-17

  One can treat a viral infection such as hepatitis B (HBV), hepatitis C (HCV), and bovine viral diarrhea virus (BVDV) infections via the delivery of pH sensitive liposomes directly into the endoplasmic reticulum (ER) membrane. Two exemplary liposome formulations are DOPE/CHEMS (DC liposomes) and DOPE/CHEMS/PEG-PE (DCPP liposomes). DC and DCPP liposomes can optimize the intracellular delivery of N-butyl deoxynojirimycin (NB-DNJ), and consequently increase the in vivo activity of this iminosugar several orders of magnitude, and could be used in combination with other therapeutic agents such as interferon and/or ribavirin. The optimized release of NB-DNJ directly into the ER can be also applied for the treatment of other viruses, for which NB-DNJ is known to be an effective antiviral, such as human immunodeficiency virus (HIV).

  人们可以通过将 pH 值敏感的脂质体直接输送到内质网（ER）膜来治疗病毒感染，如乙型肝炎（HBV）、丙型肝炎（HCV）和牛病毒性腹泻病毒（BVDV）感染。两种典型的脂质体制剂是 DOPE/CHEMS（DC 脂质体）和 DOPE/CHEMS/PEG-PE（DCPP 脂质体）。DC 和 DCPP 脂质体可优化 N-丁基脱氧野尻霉素（NB-DNJ）的细胞内递送，从而将这种亚氨基糖的体内活性提高几个数量级，并可与干扰素和/或利巴韦林等其他治疗剂结合使用。经过优化的 NB-DNJ 直接释放到 ER 中的方法也可用于治疗其他病毒，已知 NB-DNJ 是一种有效的抗病毒药物，如人类免疫缺陷病毒（HIV）。
• 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.
• A General Synthesis of Iminosugars
  作者：Ciaran McDonnell、Linda Cronin、Julie L. O'Brie、Paul V. Murphy

  DOI：10.1021/jo035763u

  日期：2004.5.1

  1-Deoxynojirimycin, 1-deoxymannojirimycin, and 1-deoxygalactostatin have been synthesized by epoxidation of tri-O-acetyl-6-deoxyhex-5-enopyranosyI azides followed by methanolysis, deacetylation, and catalytic hydrogenation. 1,6-Dideoxygalactostatin was obtained by the reaction of 2,3,4-tri-O-acetyl-6-deoxy-beta-L-arabino-hex-5-enopyranosyl azide with NIS in methanol followed by deacetylation and catalytic hydrogenation. The overall yields were 4.4-23.5% over seven to nine steps.