3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl fluoride | 163916-60-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl fluoride
• 英文别名: 2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranosyl fluoride；(2R,3S,4R,6R)-6-fluoro-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxane
• CAS: 163916-60-7
• 化学式: C₂₇H₂₉FO₄
• 分子量: 436.523
• InChiKey: ZARQOIYHRWFROL-XDZXDJIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4,5-三甲氧基苯酚 、 3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl fluoride 在 tetrafluoroboric acid 、 1-hexyl-3-methylimidazolium tetrafluoroborate 作用下， 25.0 ℃ 、266.64 Pa 条件下， 反应 1.0h， 以93%的产率得到2-[(2R,4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]-3,4,5-trimethoxyphenol
  参考文献：
  名称：

  Aryl C-glycosylation using an ionic liquid containing a protic acid

  摘要：

  Aryl C-glycosylation of several glycosyl donors, including unprotected sugars, with phenol and naphthol derivatives in an ionic liquid containing a protic acid proceeded effectively and stereoselectively to give the corresponding aryl C-glycosides in good to high yields. Because the ionic liquid was nonvolatile, the reaction could be carried out under reduced pressure; in addition, the ionic liquid could be reused without loss of effectiveness. These features contribute to the significant advantages of this novel aryl C-glycosylation reaction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.077
• 作为产物：
  描述：

  1-O-Acetyl-3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranose 在 吡啶 、 氢氟酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以92%的产率得到3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl fluoride
  参考文献：
  名称：

  Novel Stereocontrolled Glycosidations of 2-Deoxyglucopyranosyl Fluoride Using a Heterogeneous Solid Acid, Sulfated Zirconia (SO₄/ZrO₂)

  摘要：

  开发了一种新型立体选择性的2-脱氧-α-D-葡萄糖苷氟化物的糖苷化反应，采用了一种均匀且环保的固体酸——硫酸锆（SO4/ZrO2）。在25°C下，使用SO4/ZrO2在CH3CN中反应1小时，能够主要得到相应的2-脱氧-α-D-葡萄糖苷。而在0°C下，使用SO4/ZrO2与分子筛5A在乙醚中反应1小时，则能选择性地获得相应的2-脱氧-β-D-葡萄糖苷。

  DOI：

  10.1055/s-1999-2742

文献信息

• GeCl₂·Dioxane–AgBF₄ Catalyzed Activation of Glycosyl Fluorides for Glycosylation
  作者：Qiuyu Zhu、Yu Tang、Biao Yu

  DOI：10.1021/acs.orglett.2c01146

  日期：2022.5.27

  catalytic glycosyl fluoride activation system using the GeCl2·dioxane–AgBF4 combination was developed, which involves a reversible activation of the anomeric C–F bond by a [Ge(II)–Cl]+ cation and a reversible chloride ion transfer between Ge(II) and glycosyl cations. This catalytic glycosylation system is easy to operate, proceeds at room temperature, and offers a broad scope of substrates.

  开发了一种使用 GeCl 2 ·二恶烷-AgBF 4组合的催化糖基氟化物活化系统，该系统涉及通过 [Ge(II)-Cl] +阳离子对异头 C-F 键的可逆活化和在它们之间的可逆氯离子转移。 Ge(II) 和糖基阳离子。这种催化糖基化系统易于操作，在室温下进行，并提供广泛的底物。
• Recent advances in the synthesis of 2-deoxy-glycosides
  作者：Dianjie Hou、Todd L. Lowary

  DOI：10.1016/j.carres.2009.07.013

  日期：2009.10

  Glycosides of 2-deoxy-sugars, monosaccharides in which the hydroxyl group at C-2 is replaced with a hydrogen atom, occur widely in natural products and therefore have been the subject of intense synthetic activity. The report summarizes recent advances in this area, with a particular focus on work published since an earlier review on the topic, in 2000 (Marzabadi, C. H.: Franck, R. W. Tetrahedron 2000, 56, 8385-8417). (C) 2009 Elsevier Ltd. All rights reserved.
• Stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia, for the direct syntheses of α- and β-manno- and 2-deoxyglucopyranosides
  作者：Kazunobu Toshima、Hideyuki Nagai、Ken-ichi Kasumi、Kanako Kawahara、Shuichi Matsumura

  DOI：10.1016/j.tet.2004.04.071

  日期：2004.6

  Novel alpha- and beta-stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia (SO4/ZrO2), as an activator have been developed. The glycosidations of manno- and 2-deoxyglucopyranosyl alpha-fluorides with several alcohols using SO4/ZrO2 in MeCN proceeded alpha-stereoselectively, while those with the same activator in the presence of MS 5A in Et2O occurred with beta-stereo selectivity. Thus, both the alpha- and beta-manno- and 2-deoxyglucopyranosides were effectively obtained by the present glycosidations. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of Deoxy Glycosides Under Neutral Conditions in LiClO4/Solvent Mixtures
  作者：Heidrun Schene

  DOI：10.1055/s-1999-3651

  日期：1999.8
• Rare Earth Salts Promoted Glycosidation of Glycosyl Fluorides
  作者：Masakatsu Shibasaki、Won-Sup Kim、Shigeru Hosono、Hiroaki Sasai

  DOI：10.3987/com-95-s87

  日期：——