5-deoxy-L-arabinose phenylhydrazone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-deoxy-L-arabinose phenylhydrazone
• 英文别名: (1E,2S,3S,4S)-1-(phenylhydrazinylidene)pentane-2,3,4-triol
• 化学式: C₁₁H₁₆N₂O₃
• 分子量: 224.26
• InChiKey: BIVHIDUIIIYYKK-BOAFTQECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  85.1
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 5-deoxy-L-arabinose phenylhydrazone 在 吡啶 作用下， 反应 4.0h， 以98%的产率得到5-deoxy-2,3,4-O-triacetyl-L-arabinose phenylhydrazone
  参考文献：
  名称：

  Total Synthesis of l-Biopterin from l-Tartaric Acid via 5-Deoxy-l-arabinose

  摘要：

  DOI：

  10.1021/jo961426s
• 作为产物：
  描述：

  5-脱氧-L-阿拉伯糖酸GAMMA-内酯 在 二异丁基氢化铝 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 1.5h， 生成 5-deoxy-L-arabinose phenylhydrazone
  参考文献：
  名称：

  Total Synthesis of l-Biopterin from l-Tartaric Acid via 5-Deoxy-l-arabinose

  摘要：

  DOI：

  10.1021/jo961426s

文献信息

• METHOD FOR SYNTHESIZING SAPROPTERIN DIHYDROCHLORIDE
  申请人：ASYMCHEM LABORATORIES (TIANJIN)CO., LTD.

  公开号：US20150119573A1

  公开（公告）日：2015-04-30

  Disclosed is a method for synthesizing sapropterin dihydrochloride. The present disclosure reduces a synthesis route of the sapropterin dihydrochloride, and resolves a racemate intermediate or an intermediate having a low antimer isomerism value by using a chiral resolving reagent, thereby obtaining an intermediate having a high antimer isomerism value. Raw materials are cheap and readily available, and the cost is significantly reduced, hence providing an effective scheme for mass industrial production of the sapropterin dihydrochloride.

  公开了一种合成盐酸沙普曲酮的方法。本公开通过使用手性分离试剂减少了盐酸沙普曲酮的合成路线，并解决了一个具有低对映异构体值的混合物中间体或中间体，从而获得一个具有高对映异构体值的中间体。原材料价格便宜且易得，成本显著降低，因此为盐酸沙普曲酮的大规模工业生产提供了有效方案。
• METHOD OF SYNTHESIZING TETRAHYDROBIOPTERIN
  申请人：Henderson Mark

  公开号：US20090198055A1

  公开（公告）日：2009-08-06

  The present disclosure provides a method that efficiently produces (6R)-tetrahydrobiopterin in high yield and purity. The method includes the step of hydrolyzing diacetylbiopterin to biopterin under basic conditions in a biphasic mixture comprising an organic phase and an aqueous phase. After substantially complete hydrolysis of diacetylbiopterin, the aqueous phase containing biopterin can be separated from the organic phase containing most of the organic impurities, which avoids the time-consuming step of isolating biopterin as a solid. The aqueous solution containing biopterin is stereoselectively hydrogenated to (6R)-tetrahydrobiopterin under basic conditions and high hydrogen pressure in the presence of a metal catalyst (e.g., a platinum catalyst). To improve the purification of an acid addition salt of (6R)-tetrahydrobiopterin (e.g., (6R)-tetrahydrobiopterin dihydrochloride), any residual salts (e.g., sodium salts) in the aqueous solution after the hydrogenation reaction can be removed by contacting the aqueous solution with an ion (e.g., cation) exchange resin or column. Alternatively, removal of residual salts from the aqueous solution can be omitted if an organic amine (e.g., diethylamine or triethylamine) rather than an inorganic base is used in the hydrolysis and/or hydrogenation reactions.

  本公开提供了一种高效地在高产率和纯度下生产(6R)-四氢生物蝶啶的方法。该方法包括在包含有机相和水相的两相混合物中，在碱性条件下水解二乙酰生物蝶啶至生物蝶啶的步骤。在二乙酰生物蝶啶基本完全水解后，含有生物蝶啶的水相可以与含有大部分有机杂质的有机相分离，避免了将生物蝶啶分离为固体的耗时步骤。含有生物蝶啶的水溶液在碱性条件和高氢压下，在金属催化剂的存在下（例如，铂催化剂）立体选择性地氢化为(6R)-四氢生物蝶啶。为了提高对(6R)-四氢生物蝶啶的酸盐（例如，(6R)-四氢生物蝶啶二盐酸盐）的纯化，可以通过将氢化反应后水溶液中的任何残留盐（例如，钠盐）与离子（例如，阳离子）交换树脂或柱接触来去除。另外，如果在水解和/或氢化反应中使用有机胺（例如，二乙胺或三乙胺）而不是无机碱，则可以省略从水溶液中去除残留盐的步骤。
• Method for producing L-biopterin
  申请人：Tazawa Shinnosuke

  公开号：US20060142573A1

  公开（公告）日：2006-06-29

  To provide a method for producing L-biopterin on a large industrial scale by using a reagent which is inexpensive and easy to handle, without requiring a use of any particular equipment or plants.

  通过使用价格便宜且易于处理的试剂，在不需要使用任何特殊设备或工厂的情况下，为大规模工业生产L-生物蝶啶提供一种方法。
• COMPOSITIONS AND METHODS FOR THE TREATMENT OF METABOLIC DISEASES
  申请人：CELLIXBIO PRIVATE LIMITED

  公开号：US20150291590A1

  公开（公告）日：2015-10-15

  The invention relates to the compounds of formula I, formula II and formula III or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, formula II or formula III; and methods for treating or preventing metabolic diseases may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of phenylketonuria, cardiovascular disease, autism, ADHD, hypertension, endothelial dysfunction and chronic kidney disease.

  该发明涉及公式I、公式II和公式III的化合物或其药用可接受的盐，以及其多晶型、溶剂合物、对映体、立体异构体和水合物。包括公式I、公式II或公式III化合物的有效量的药物组合物；以及用于治疗或预防代谢性疾病的方法可以制备成口服、颊内、直肠、局部、经皮、经粘膜、静脉、肠道、糖浆或注射剂。这些组合物可用于治疗苯丙酮尿症、心血管疾病、自闭症、注意力缺陷多动障碍、高血压、内皮功能障碍和慢性肾脏疾病。
• Process for preparing biopterin and its derivatives
  申请人：KANEGAFUCHI KAGAKU KOGYO KABUSHIKI KAISHA

  公开号：EP0079574A1

  公开（公告）日：1983-05-25

  A novel compound, 1',2'-diacyl-(6R,S)-5,6,7,8-tetrahydro-L-biopterin which is prepared by catalytical hydrogenation of a 1',2'-diacyl-L-biopterin in a solvent in the presence of a catalyst. The 1',2'-diacyl-L-biopterin is prepared from a 1,1-dialkylsulfonyl-L- rhamnose through an acyl derivative of 5-deoxy-L-arabinose and a hydrazine derivative of tetrahydro-L-biopterin without isolating the intermediate products. The 1',2'-diacyl-(6R,S)-5,6,7,8-tetrahydro-L-biopterin can be used for treatment of atypical phenylketonuria or dihydropterin-reductase deficiency and can readily cross the blood brain barrier without neurotransmitter precursors.

  一种新型化合物--1',2'-二乙酰基-(6R,S)-5,6,7,8-四氢-L-生物蝶呤，是在催化剂存在下，在溶剂中通过催化氢化 1',2'-二乙酰基-L-生物蝶呤而制备的。1',2'-二乙酰基-L-生物蝶呤由 1,1-二烷基磺酰基-L-鼠李糖通过 5-脱氧-L-阿拉伯糖的酰基衍生物和四氢-L-生物蝶呤的肼衍生物制备而成，中间产物无需分离。这种 1',2'-二乙酰基-(6R,S)-5,6,7,8-四氢-L-生物蝶呤可用于治疗非典型苯丙酮尿症或二氢蝶呤还原酶缺乏症，并且不含神经递质前体，可轻易通过血脑屏障。