3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-hexopyranosyl fluoride | 134175-79-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-hexopyranosyl fluoride
• 英文别名: 3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl fluoride；[(2R,3S,4R,6S)-3,4-diacetyloxy-6-fluorooxan-2-yl]methyl acetate
• CAS: 134175-79-4
• 化学式: C₁₂H₁₇FO₇
• 分子量: 292.261
• InChiKey: PJFDRXZHHIFONB-KKOKHZNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  双丙酮半乳糖 、 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-hexopyranosyl fluoride 生成 1,2:3,4-di-O-isopropylidene-6-O-(3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-hexopyranosyl)-α-D-galactopyranose
  参考文献：
  名称：

  JUNNEMANN, JOSEF;LUNDT, INGE;THIEM, JOACHIM, LIEBIGS ANN. CHEM.,(1991) N, C. 759-764

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4,6-O-三乙酰基-2-脱氧-D-葡萄糖 以75%的产率得到
  参考文献：
  名称：

  JUNNEMAN, JOSEF;LUNDT, INGE;THIEM, JOACHIM, ACTA CHEM. SCAND., 45,(1991) N, C. 494-498

  摘要：

  DOI：

文献信息

• Organofluorine Compounds and Fluorinating Agents; 18:1 Trifluoromethylzinc Bromide as a Reagent for the Preparation of Glycosyl Fluorides
  作者：Ralf Miethchen、Christian Hager、Martin Hein

  DOI：10.1055/s-1997-3181

  日期：1997.2

  Trifluoromethylzinc bromide was used to prepare the corresponding glycosyl fluorides from the peracetylated α-pyranosyl bromides of D-glucose 1, D-galactose 3, D-mannose 5, D-lyxose 7, and L-rhamnose 9, respectively, in good yields. D-Glucopyranosyl bromide 1 and the D-galactopyranosyl bromide 3, exclusively delivered the corresponding β-D-glycosyl fluorides 2 β and 4 β. The other bromides 5, 7 and 9 formed mixtures of anomeric fluorides (6 α/6 β, 8 α/8 β, 10 α/10 β). Similarly, the anomeric OH-groups of the D-glycopyranoses 11, 12, 13, 15, 17 could be substituted by fluoride using trifluoromethylzinc bromide/titanium tetrafluoride. In all cases mixtures of anomeric fluorides 2 α/2 β, 6 α/6 β, 14 α/14 β, 16 α/16 β, and 18 α/18 β were obtained.

  三氟甲基锌溴化物被用于从D-葡萄糖 1、D-半乳糖 3、D-甘露糖 5、D-木糖 7和L-鼠李糖 9的全乙酰化α-吡喃硫基溴化物制备相应的糖基氟化物，并获得良好产率。D-葡萄吡喃硫基溴化物 1和D-半乳糖吡喃硫基溴化物 3，单独生成相应的β-D-糖基氟化物 2 β和4 β。其他溴化物 5、7和9形成了古典氟化物的混合物（6 α/6 β，8 α/8 β，10 α/10 β）。类似地，D-吡喃糖 11、12、13、15、17的构型异构体OH-基团也可以通过三氟甲基锌溴化物/四氟化钛进行氟化。在所有情况下，得到的都是古典氟化物的混合物 2 α/2 β，6 α/6 β，14 α/14 β，16 α/16 β，以及 18 α/18 β。
• Direct <i>C</i>-Glycosylation of Organotrifluoroborates with Glycosyl Fluorides and Its Application to the Total Synthesis of (+)-Varitriol
  作者：Jing Zeng、Seenuvasan Vedachalam、Shaohua Xiang、Xue-Wei Liu

  DOI：10.1021/ol102473k

  日期：2011.1.7

  C-glycosides via BF3·Et2O promoted coupling of organotrifluoroborates and glycosyl fluorides is reported. The application of this method was further demonstrated by the concise and efficient total synthesis of (+)-varitriol in only seven steps.

  据报道，通过BF 3 ·Et 2 O促进了有机三氟硼酸酯和糖基氟化物的偶联，采用了温和，立体选择性和快速的方法访问炔基和烯基C-糖苷。该方法的应用通过仅七个步骤的简明有效的全合成（+）-varitriol进一步得到了证明。
• Preparation of 1-fluoroglycosides from 1-arylthio and 1-arylselenoglycosides using 4-methyl(difluoroiodo)benzene
  作者：S. Caddick、L. Gazzard、W.B. Motherwell、J.A. Wilkinson

  DOI：10.1016/0040-4020(95)00889-g

  日期：1996.1

  Treatment of readily available thio- and selenoglycosides with the reagent 4-methyl(difluoroiodo)benzene leads to the formation of the corresponding fluoroglycosides in moderate to good yield.
• Juenneman, Josef; Lundt, Inge; Thiem, Joachim, Acta Chemica Scandinavica, 1991, vol. 45, # 5, p. 494 - 498
  作者：Juenneman, Josef、Lundt, Inge、Thiem, Joachim

  DOI：——

  日期：——
• Juennemann, Josef; Lundt, Inge; Thiem, Joachim, Liebigs Annalen der Chemie, 1991, # 8, p. 759 - 764
  作者：Juennemann, Josef、Lundt, Inge、Thiem, Joachim

  DOI：——

  日期：——