6-Deoxy-6-fluoro-α-D-galactopyranose | 143616-86-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-Deoxy-6-fluoro-α-D-galactopyranose
• 英文别名: 6-deoxy-6-fluorogalactopyranose；6-fluoro-D-6-deoxy-galactose；6-fluoro-α-D-6-deoxy-galactopyranose；6-Deoxy-6-fluoro-α-D-galaktopyranose；6-Fluor-6-desoxy-α-D-galactose；6-Fluor-6-deoxy-α-D-galaktose；(2S,3R,4S,5R,6S)-6-(fluoromethyl)oxane-2,3,4,5-tetrol
• CAS: 143616-86-8
• 化学式: C₆H₁₁FO₅
• 分子量: 182.149
• InChiKey: SHFYXYMHVMDNPY-PHYPRBDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 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：

  6-Deoxy-6-fluoro-α-D-galactopyranose 在 钾硼氢 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 1-fluoro-L-1-deoxy-galactitol
  参考文献：
  名称：

  Fluorocarbohydrates

  摘要：

  DOI：

  10.1016/s0008-6215(00)85738-9
• 作为产物：
  描述：

  6-deoxy-6-fluoro-2,3,5-tri-O-trimethylsilyl-D-galactofuranose 在 甲酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 6-Deoxy-6-fluoro-α-D-galactopyranose 、 6-Deoxy-6-fluoro-β-D-galactopyranose 、 (2R,3R,4R,5R)-5-[(1S)-2-fluoro-1-hydroxyethyl]oxolane-2,3,4-triol 、 (2S,3R,4R,5R)-5-[(1S)-2-fluoro-1-hydroxyethyl]oxolane-2,3,4-triol
  参考文献：
  名称：

  Developing an asymmetric, stereodivergent route to selected 6-deoxy-6-fluoro-hexoses

  摘要：

  自由基溴化和亲核氟化可将山梨酸甲酯转化为 6-氟类似物，并进行连续的不对称二羟基化反应。通过使用不同的配体组合制备了一系列 6-脱氧-6-氟糖。虽然获得的对映体过量与其他 6-取代山梨酸酯的对映体过量相当，但二羟基化的区域选择性适中，同时获得了 2,3- 和 4,5- 二醇。开发了一种成功的临时全硅烷化策略，将二羟基化产物快速转化为氟糖6-脱氧-6-氟-L-艾糖、6-氟-L-岩藻糖和6-脱氧-6-氟-D-半乳糖，这由 6-氟-六-2E,4E-二烯酸甲酯 6 得到的总产率为 4%、6% 和 8%。

  DOI：

  10.1039/b815342f

文献信息

• 1(Beta-D-Glycopyranosyl)-3-Substituted Nitrogenous Heterocyclic Compound, Medicinal Composition Containing the Same, and Medicinal Use Thereof
  申请人：Teranishi Hirotaka

  公开号：US20080139484A1

  公开（公告）日：2008-06-12

  A compound having SGLT1 and/or SGLT2 inhibitory activity which is usable as an agent for the prevention or treatment of diabetes, postprandial hyperglycemia, impaired glucose tolerance, diabetic complications, obesity, etc. It is a 1-(β-D-glycopyranosyl)-3-substituted nitrogen-containing heterocyclic compound represented by the general formula (I), a prodrug, or a pharmaceutically acceptable salt thereof, or a hydrate or solvate thereof; an SGLT inhibitor containing the same; a pharmaceutical composition containing the same and a medicinal use thereof. In the formula, ring A represents optionally substituted aryl or heteroaryl; Q 1 to Q 5 independently represent a carbon atom having a hydrogen atom or substituent bonded thereto or a nitrogen atom; E represents a single bond, alkylene, —O—, —S— or —NH—; and R represents methyl, ethyl, fluoromethyl or hydroxymethyl.

  具有SGLT1和/或SGLT2抑制活性的化合物，可用作预防或治疗糖尿病、餐后高血糖、糖耐量受损、糖尿病并发症、肥胖等的药物。该化合物是一种1-(β-D-葡萄糖苷基)-3-取代的含氮杂环化合物，由通式(I)表示，是一种前药、药学上可接受的盐或其水合物或溶剂化物；还包括含有该化合物的SGLT抑制剂、含有该化合物的药物组合物和药用。在式中，环A代表可选取代的芳基或杂环基；Q1至Q5独立地表示具有氢原子或配基键合的碳原子或氮原子；E代表单键，烷基，-O-，-S-或-NH-；R代表甲基，乙基，氟甲基或羟甲基。
• 1-( -D-GLYCOPYRANOSYL)-3-SUBSTITUTED NITROGENOUS HETEROCYCLIC COMPOUND, MEDICINAL COMPOSITION CONTAINING THE SAME, AND MEDICINAL USE THEREOF
  申请人：Kissei Pharmaceutical Co., Ltd.

  公开号：EP1803729A1

  公开（公告）日：2007-07-04

  A compound having SGLT1 and/or SGLT2 inhibitory activity which is usable as an agent for the prevention or treatment of diabetes, postprandial hyperglycemia, impaired glucose tolerance, diabetic complications, obesity, etc. It is a 1-(β-D-glycopyranosyl)-3-substituted nitrogen-containing heterocyclic compound represented by the general formula (I), a prodrug, or a pharmaceutically acceptable salt thereof, or a hydrate or solvate thereof; an SGLT inhibitor containing the same; a pharmaceutical composition containing the same and a medicinal use thereof. In the formula, ring A represents optionally substituted aryl or heteroaryl; Q1 to Q5 independently represent a carbon atom having a hydrogen atom or substituent bonded thereto or a nitrogen atom; E represents a single bond, alkylene, -O-, -S- or -NH-; and R.represents methyl, ethyl, fluoromethyl or hydroxymethyl.

  一种具有 SGLT1 和/或 SGLT2 抑制活性的化合物，可用作预防或治疗糖尿病、餐后高血糖症、糖耐量受损、糖尿病并发症、肥胖症等的药物。它是由通式（I）代表的1-（β-D-吡喃甘露糖基）-3-取代的含氮杂环化合物、其原药或药学上可接受的盐，或其水合物或溶液；含有相同物质的SGLT抑制剂；含有相同物质的药物组合物及其药用用途。式中，环A代表任选取代的芳基或杂芳基；Q1至Q5独立地代表具有氢原子或取代基键合的碳原子或氮原子；E代表单键、亚烷基、-O-、-S-或-NH-；R.代表甲基、乙基、氟甲基或羟甲基。
• Developing an asymmetric, stereodivergent route to selected 6-deoxy-6-fluoro-hexoses
  作者：Audrey Caravano、Robert A. Field、Jonathan M. Percy、Giuseppe Rinaudo、Ricard Roig、Kuldip Singh

  DOI：10.1039/b815342f

  日期：——

  Free radical bromination and nucleophilic fluorination allows the conversion of methyl sorbate into the 6-fluoro analogue which undergoes sequential asymmetric dihydroxylation reactions. A range of 6-deoxy-6-fluorosugars were prepared by using different combinations of ligands. While the enantiomeric excesses obtained were comparable to those from other 6-substituted sorbates, the regioselectivity of dihydroxylation was moderate, with both 2,3- and 4,5-diols being obtained. A successful temporary persilylation strategy was evolved to convert the products of dihydroxylation rapidly to the fluorosugars 6-deoxy-6-fluoro-L-idose, 6-fluoro-L-fucose and 6-deoxy-6-fluoro-D-galactose, which were obtained in overall yields of 4%, 6% and 8% from methyl 6-fluoro-hexa-2E,4E-dienoate 6.

  自由基溴化和亲核氟化可将山梨酸甲酯转化为 6-氟类似物，并进行连续的不对称二羟基化反应。通过使用不同的配体组合制备了一系列 6-脱氧-6-氟糖。虽然获得的对映体过量与其他 6-取代山梨酸酯的对映体过量相当，但二羟基化的区域选择性适中，同时获得了 2,3- 和 4,5- 二醇。开发了一种成功的临时全硅烷化策略，将二羟基化产物快速转化为氟糖6-脱氧-6-氟-L-艾糖、6-氟-L-岩藻糖和6-脱氧-6-氟-D-半乳糖，这由 6-氟-六-2E,4E-二烯酸甲酯 6 得到的总产率为 4%、6% 和 8%。
• Fluorocarbohydrates
  作者：P.W. Kent、J.R. Wright

  DOI：10.1016/s0008-6215(00)85738-9

  日期：1972.4