2-deoxy-2-fluoro-α-D-galactopyranosyl fluoride | 75414-46-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-2-fluoro-α-D-galactopyranosyl fluoride
• 英文别名: (2R,3R,4S,5R,6R)-5,6-difluoro-2-(hydroxymethyl)oxane-3,4-diol
• CAS: 75414-46-9
• 化学式: C₆H₁₀F₂O₄
• 分子量: 184.14
• InChiKey: YZRDPODBASCWCK-DVKNGEFBSA-N

物化性质

• 沸点：
  327.9±42.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.27
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.92
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-deoxy-2-fluoro-α-D-galactopyranosyl fluoride 在 氢溴酸 、 sodium methylate 、 silver trifluoromethanesulfonate 、 氢气 、 溶剂黄146 、 silver carbonate 作用下， 以 乙醇 、 乙酸酐 、 乙腈 为溶剂， 反应 3.5h， 生成 4-O-(2-deoxy-2-fluoro-β-D-galactopyranosyl)-D-glucopyranose
  参考文献：
  名称：

  Design and Synthesis of 2‘-Deoxy-2‘-Fluorodisaccharides as Mechanism-Based Glycosidase Inhibitors That Exploit Aglycon Specificity

  摘要：

  Stable, aglycon-specific inactivators of glycosidases have considerable potential as fools in the study of mechanisms of oligosaccharide processing, and possibly as avenues toward new therapeutics. Glycosidases for which the rate-determining step with the natural substrate is the hydrolysis of the glycosyl-enzyme intermediate are shown to be inactivated by the 2'-deoxy-2'-fluoro derivative of this substrate. Thus Agrobacterium faecalis beta-glucosidase is inactivated by 2'-deoxy-2'-fluorocellobiose according to inactivation parameters of k(i) = 0.018 min(-1) and K-i = 20 mM. Inactivation is shown to occur via the accumulation of the same 2-deoxy-2-fluoroglycosyl-enzyme intermediate as that formed using activated 2-deoxy-2-fluoroglycosides by identification of the labeled peptide in proteolytic digests. Thus, interactions between the enzyme and the sugar aglycon provide sufficient transition state stabilization to allow formation and trapping of the glycosyl-enzyme. beta-Glucocerebrosidase, a beta-glucosidase specific for hydrolysis of glucocerebrosides, is not inactivated by 2'-deoxy-2'-fluorocellobiose, thereby demonstrating the aglycon specificity of this class of inactivator.

  DOI：

  10.1021/ja9627454
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-galactopyranosyl fluoride 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以77%的产率得到2-deoxy-2-fluoro-α-D-galactopyranosyl fluoride
  参考文献：
  名称：

  使用氟化氙方便地合成1,2-二氟-1,2-二脱氧己糖

  摘要：

  已经显示了在BF 3存在下使用XeF 2将氟添加到乙酰化的缩醛中的双键上的方法，为合成乙酰化的1、2-二脱氧-1、2-二氟糖提供了便利的途径。该试剂主要从受阻最小的一侧进攻双键，形成顺式加合物，但该反应还提供了其他异构体，这些异构体已通过色谱法分离，其立体化学由19F NMR光谱。所提出的反应机理涉及试剂对C-2的初始亲电子攻击，然后是对C-1的亲核攻击。加合物的脱乙酰基得到1,2-二脱氧基-1,2-二氟糖，这在生化研究中是有意义的。通过选择性水解1，2-二脱氧-1，2-二氟-1-岩藻糖的异头氟原子来制备结晶的2-脱氧-2-1-岩藻糖。

  DOI：

  10.1016/0040-4020(82)85090-4

文献信息

• Synthesis of 2-deoxy-2-fluorohexoses by fluorination of glycals in aqueous media
  作者：Mirko Diksic、Dean Jolly

  DOI：10.1016/s0008-6215(00)90191-5

  日期：1986.9

  and organic solvent-water with molecular fluorine and, for 18 F-labelled compounds, with [ 18 F]fluorine. Chemical yields of 40 and 10% were obtained for 2-deoxy-2-fluoro- d -glucose and 2-deoxy-2-fluoro- d -mannose, respectively, and 35 and 5% for 2-deoxy-2-fluoro- d -galactose ( 12 ) and 2-deoxy-2-fluoro- d -talose ( 13 ), respectively. In the fluorination of 3 , the chemical yields of 12 and 13 were

  摘要1,5-Anhydro-2-deoxy- d-arabino-（d -glucal），1,5-anhydro-2-deoxy- d-lyxo-（d -galactal）和3,4,6-tri-在水中和有机溶剂中对O-乙酰基1,5,5-脱水-2-脱氧-d-lyxo-己-1-烯醇（3,4,6-tri-O-乙酰基-d-半乳糖）（3）进行氟化-具有分子氟的水，以及对于18 F标记的化合物，具有[18 F]氟。2-脱氧-2-氟-d-葡萄糖和2-脱氧-2-氟-d-甘露糖的化学收率分别为40％和10％，2-脱氧-2-氟-d-甘露糖的化学收率分别为35％和5％。 d-半乳糖（12）和2-脱氧-2-氟-d-塔洛糖（13）。在氟化3中，化学产率12和13分别为38和6％。描述了2-脱氧-2-氟-d-己糖的1c分离。
• Reactions of glycals with xenon fluoride: an improved synthesis of 2-deoxy-2-fluorosaccharides
  作者：W. Korytnyk、S. Valentekovic-Horvat

  DOI：10.1016/s0040-4039(00)92755-2

  日期：1980.1

  The 1,2-double bond in acetylated glycals has been fluorinated with XeF2 in the presence of BF3 to give 1,2-deoxy-1,2-difluorosaccharides. A mechanism for this reaction has been proposed. This method represents an improvement in the synthesis of 2-deoxy-2-fluorosaccharides.

  在BF 3的存在下，已用XeF 2氟化了乙酰化缩醛中的1,2-双键，得到1,2-脱氧-1,2-二氟糖。已经提出了该反应的机制。该方法代表了2-脱氧-2-氟糖合成的一种改进。
• Preparation of two methyl deoxyfluoro-β-d-galactopyranosides, and their interaction with galactan-specific immunoglobulin A 1539 (fab′)
  作者：Yitzhak Ittah、Cornelis P.J. Glaudemans

  DOI：10.1016/s0008-6215(00)85575-5

  日期：1981.9

  Methyl 2-deoxy-2-fluoro-beta-D-glactopyranoside (2) and methyl 4-deoxy-4-fluoro-beta-D-glactopyranoside (7) have been prepared, and the possibility of their binding to (1 leads to 6)-beta-D-galactopyranan-specific immunoglobulin A J539 (Fab') has been investigated. Compound 2 does not show binding, whereas 7 does. It appears that the 2-hydroxyl group of methyl beta-D-galactopyranoside may take part in hydrogen bonding to the protein.