galactose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: galactose
• 英文别名: (3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal
• 化学式: C₆H₁₂O₆
• 分子量: 180.158
• InChiKey: GZCGUPFRVQAUEE-SJLAOBFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-塔格糖 在 2-氨基吡啶 、 溶剂黄146 作用下， 生成 galactose
  参考文献：
  名称：

  Development of a chemical strategy to produce rare aldohexoses from ketohexoses using 2-aminopyridine

  摘要：

  Rare sugars are monosaccharides that are found in relatively low abundance in nature. Herein, we describe a strategy for producing rare aldohexoses from ketohexoses using the classical Lobry de Bruyn-Alberda van Ekenstein transformation. Upon Schiff-base formation of keto sugars, a fluorescence-labeling reagent, 2-aminopyridine (2-AP), was used. While acting as a base catalyst, 2-AP efficiently promoted the ketose-to-aldose transformation, and acting as a Schiff-base reagent, it effectively froze the ketose-aldose equilibrium. We could also separate a mixture of Sor, Gul, and Ido in their Schiff-base forms using a normal-phase HPLC separation system. Although Gul and Ido represent the most unstable aldohexoses, our method provides a practical way to rapidly obtain these rare aldohexoses as needed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.09.021

文献信息

• PROCESS FOR PRODUCING CARBON-DIMINISHED ALDOSE COMPOUND
  申请人：Asubio Pharma Co., Ltd.

  公开号：EP1849793A1

  公开（公告）日：2007-10-31

  The present invention provides a process capable of industrially producing 5-deoxy-L-arabinose, important as a raw material for the production of sapropterin useful as a therapeutic agent for atypical hyperphenylalaninemia, satisfactorily efficiently even with a simple production apparatus. Provided is the process for producing 5-deoxy-L-arabinose characterized by including: reacting L-rhamnose with a C11-16 straight chain alkyl mercaptan compound in the presence of an acid catalyst to prepare L-rhamnose dialkylmercaptal; subjecting then the obtained compound to an oxidation reaction to prepare a sulfonyl derivative; and subjecting then the sulfonyl derivative to a carbon-reduction reaction to prepare 5-deoxy-L-arabinose. The present production process can also be applied to a process for producing compounds obtained by removing one carbon atom from other aldol compounds, and thus the present invention provides a general process for producing compounds obtained by reducing the number of carbon atoms from aldose compounds.

  本发明提供了一种工业生产5-去氧-L-阿拉伯糖的方法，该方法是生产治疗非典型高苯丙氨酸血症的治疗剂Sapropterin的原材料，即使使用简单的生产设备也能高效地生产。该生产方法包括以下步骤：在酸催化剂的存在下，将L-鼠李糖与C11-16直链烷基巯基化合物反应，制备L-鼠李糖二烷基硫代缩醛；然后将所得化合物进行氧化反应，制备磺酰基衍生物；最后将磺酰基衍生物进行碳还原反应，制备5-去氧-L-阿拉伯糖。该生产方法也可以应用于从其他醛糖化合物中去除一个碳原子得到的化合物的生产过程，因此本发明提供了一种从醛糖化合物中减少碳原子数量得到化合物的通用生产方法。