(3R,4S,5S,6R)-2-fluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol | 447-27-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5S,6R)-2-fluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• 英文别名: Glucosyl fluoride；(3R,4S,5S,6R)-2-fluoro-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 447-27-8
• 化学式: C₆H₁₁FO₅
• 分子量: 182.149
• InChiKey: ATMYEINZLWEOQU-GASJEMHNSA-N

物化性质

• 沸点：
  371.3±42.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,6R)-2-fluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 、 甜叶悬钩子苷 在 F-1-glucose-dependent glycosynthase Bgl₃ E₃₈₃A from glycosidase Bgl₃ 作用下， 以 aq. buffer 为溶剂， 以96.7%的产率得到rebaudioside G
  参考文献：
  名称：

  Enzymatic Monoglucosylation of Rubusoside and the Structure–Sweetness/Taste Relationship of Monoglucosyl Derivatives

  摘要：

  Monoglucosylation of rubusoside not only could increase its structural diversity but may also improve its taste. To biosynthesize the monoglucosyl rubusosides, a series of glycosyltransferases and glycosynthases were screened to identify the enzymes capable of specifically glycosylating the hydroxyl groups of the 13-O-beta-D-glucosyl and 19-COO-beta-D-glucosyl moieties. After structural characterization, the effect of structure on sweetness and taste was established based on these rubusoside-derived analogues, including two first characterized compounds. beta-Monoglucosylation of two 2-hydroxyl groups, as well as alpha-monoglucosylations of the 4- and 6-hydroxyl groups of the 13-glucosyl moiety, could significantly increase the relative sweetness of rubusoside to 140 while maintaining or improving the taste quality. In contrast, monoglucosylations of other hydroxyl groups in our study usually decreased the taste quality of the rubusoside. Additionally, the possibility of a negative influence of these monoglucosylated derivatives on the function of islets was preliminarily excluded, which should facilitate the development of rubusoside-derived sweeteners.

  DOI：

  10.1021/acs.jafc.0c03236
• 作为产物：
  描述：

  、 葡萄糖 、 氢氟酸 反应 2.5h， 以9.5 g of glucosyl fluoride were obtained的产率得到(3R,4S,5S,6R)-2-fluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Process for the single-stage preparation of glycosyl fluorides

  摘要：

  一种通过将糖类溶解在液态氢氟酸中并蒸发氢氟酸来单步制备糖基氟化物的方法，其中所得的糖基氟化物被隔离出来，当在相对较高的温度下开始蒸发氢氟酸时，通常在-20℃至+20℃之间，以高蒸发速率进行蒸发，或者在蒸发开始时使用低蒸发速率时，设置足够低的温度，通常在-80℃至-30℃之间。

  公开号：

  US04847372A1

文献信息

• [EN] PROCESSES FOR THE PRODUCTION OF XYLITOL<br/>[FR] PROCEDES DE PRODUCTION DE XYLITOL
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：WO2005095314A1

  公开（公告）日：2005-10-13

  Methods of producing xylitol comprising the oxidative decarboxylation of a reactant substrate are provided herein. The oxidative decarboxylation is performed in one of two ways. In the first, the oxidative decarboxylation is performed by an electrochemical process, preferably an anodic odixative decarboxylation of a reactant substrate. In the second, the oxidative decarboxylation of the reactant substrate is carried out by a series of oxidation-reduction chemical reactions.

  本文提供了一种生产木糖醇的方法，包括对反应底物进行氧化脱羧。氧化脱羧可以通过两种方式之一进行。在第一种方式中，氧化脱羧是通过电化学过程进行的，最好是对反应底物进行阳极氧化脱羧。在第二种方式中，对反应底物的氧化脱羧是通过一系列氧化还原化学反应进行的。
• NEW C-GLYCOSYLPOLYPHENOL ANTIDIABETIC AGENTS, EFFECT ON GLUCOSE TOLERANCE AND INTERACTION WITH BETA-AMYLOID. THERAPEUTIC APPLICATIONS OF THE SYNTHESIZED AGENT(S) AND OF GENISTA TENERA ETHYL ACETATE EXTRACTS CONTAINING SOME OF THOSE AGENTS
  申请人：UNIVERSIDADE DE LISBOA

  公开号：US20150031639A1

  公开（公告）日：2015-01-29

  The present invention concerns the antidiabetic-activity of compounds type A, namely of 8-β-D-glucosylgenistein, which is not toxic to eukaryotic cells and has demonstrated to produce complete normalization of fasting hyperglycaemia, to reduce excessive postprandial glucose excursion, to increase glucose-induced insulin secretion and insulin sensitivity. An alternative synthesis for this molecular entity and its binding ability to β-amyloid oligomers is also included in the present invention, which also comprises Genista tenera ethyl acetate extract for use as antihyperglycaemic, agent i.e. for lowering blood glucose levels in mammals that are pre-diabetic or have type 2 or type 1 diabetes. The inhibitory activity of α-glucosidase by Genista tenera ethyl acetate and butanol extracts and that of glucose-6-phosphatase by these two extracts and the diethyl ether plant extract is also part of the present invention.

  本发明涉及A型化合物的抗糖尿病活性，即8-β-D-葡萄糖基异黄酮的抗糖尿病活性。该化合物对真核细胞无毒，并已证明能完全正常化空腹高血糖，减少过度餐后血糖波动，增加葡萄糖诱导的胰岛素分泌和胰岛素敏感性。本发明还包括该分子实体的另一种合成方法以及其与β-淀粉样寡聚体的结合能力，同时还包括Genista tenera乙酸乙酯提取物用作抗高血糖剂，即用于降低处于糖尿病前期或已患2型或1型糖尿病的哺乳动物的血糖水平。本发明还包括Genista tenera乙酸乙酯和丁醇提取物的α-葡萄糖苷酶抑制活性以及这两种提取物和乙醚植物提取物的葡萄糖-6-磷酸酶抑制活性。
• [EN] PREPARATION OF GLUCOSAMINYL MURAMIC ACID DERIVATIVES<br/>[FR] PREPARATION DE DERIVES D'ACIDE MURAMIQUE DE GLUCOSAMINYLE
  申请人：ENDOREX CORPORATION

  公开号：WO1997012894A1

  公开（公告）日：1997-04-10

  (EN) The present invention provides a method for the preparation of disaccharides, such as glucosaminyl muramic acids peptides and derivatives. The method includes condensing a protected muramic acid ester with a 1-organothio- or 1-fluoroglucosamine derivative in the presence of a suitable promoter to produce a protected glucosaminyl muramic acid ester. The protected glucosaminyl muramic acid ester may be used to prepare disaccharide peptides, such as N-acetylglucosaminyl-N-acetylmuramyl dipeptides, which have demonstrated immunological activity. Protected muramic acid esters and 1-organothio- or 1-fluoro-glucosamine compounds which may be employed as intermediates in the method are also provided.(FR) L'invention concerne un procédé de préparation de disaccharides, tels que des peptides et des dérivés d'acide muramique de glucosaminyle. Ce procédé consiste à condenser un ester protégé d'acide muramique avec un dérivé de 1-organothio- ou 1-fluoroglucosamine en présence d'un promoteur approprié, de manière à obtenir un ester protégé d'acide muramique de glucosaminyle. On peut utiliser cet ester protégé afin de préparer des peptides de disaccharides, tels que des dipeptides de N-acétylglucosaminyl-N-acétylmuramyle, qui se sont avérés présenter une activité immunologique. L'invention concerne également des esters protégés d'acide muramique et des composés de 1-organothio- ou 1-fluoroglucosamine que l'on peut utiliser en tant qu'intermédiaires dans le procédé.

  本发明提供了一种制备二糖的方法，例如葡萄糖氨基酰麻酸肽和衍生物。该方法包括在适当的促进剂存在下，将保护的麻酸酯与1-有机硫基或1-氟葡萄糖胺衍生物缩合，以产生保护的葡萄糖氨基麻酸酯。保护的葡萄糖氨基麻酸酯可用于制备二糖肽，例如N-乙酰葡萄糖氨基酰-N-乙酰麻酰二肽，其已经表现出免疫活性。还提供了可用作中间体的保护麻酸酯和1-有机硫基或1-氟葡萄糖胺化合物。
• Processes for the production of xylitol
  申请人：BeMiller N. James

  公开号：US20050272961A1

  公开（公告）日：2005-12-08

  Methods of producing xylitol comprising the oxidative decarboxylation of a reactant substrate are provided herein. The oxidative decarboxylation is performed in one of two ways. In the first, the oxidative decarboxylation is performed by an electrochemical process, preferably an anodic odixative decarboxylation of a reactant substrate. In the second, the oxidative decarboxylation of the reactant substrate is carried out by a series of oxidation-reduction chemical reactions.

  本文提供了通过反应底物的氧化脱羧反应来生产木糖醇的方法。氧化脱羧反应有两种方式。第一种是通过电化学过程进行氧化脱羧反应，最好是反应底物的阳极氧化脱羧反应。第二种是通过一系列的氧化还原化学反应来进行反应底物的氧化脱羧反应。
• Solid- and solution-phase synthesis of heparin and other glycosaminoglycans
  申请人：Seeberger H. Peter

  公开号：US20050187381A1

  公开（公告）日：2005-08-25

  Described is a modular, general synthetic strategy for the preparation in solution and on a solid support of heparin, heparin-like glycosaminoglycans, glycosaminoglycans and non-natural analogs of each of them. Additionally, the modular strategy provides the basis for the preparation of combinatorial libraries and parallel libraries of defined glycosaminoglycan oligosaccharides. The defined glycosaminoglycan structures may be used in high-throughput screening experiments to identify carbohydrate sequences that regulate a host of recognition and signal-transduction processes. The determination of specific sequences involved in receptor binding holds great promise for the development of molecular tools which will allow modulation of processes underlying viral entry, angiogenesis, kidney diseases and diseases of the central nervous system. Notably, the present invention enables the automated synthesis of glycosaminoglycans in much the same fashion that peptides and oligonucleotides are currently assembled.

  本文介绍了一种模块化的、通用的合成策略，用于在溶液和固相支持上制备肝素、类肝素的糖胺聚糖、糖胺聚糖和它们的非天然类似物。此外，这种模块化策略为定义的糖胺聚糖寡糖的组合式库和并行式库的制备提供了基础。这些定义的糖胺聚糖结构可以用于高通量筛选实验，以识别调节多种识别和信号传导过程的碳水化合物序列。确定参与受体结合的特定序列对于开发分子工具来调节病毒进入、血管生成、肾脏疾病和中枢神经系统疾病的过程具有巨大的前景。值得注意的是，本发明使糖胺聚糖的自动化合成方式与目前蛋白质和寡核苷酸的组装方式非常相似。