3,4-isopropylidene-2-fluoro-2-O-methyl-D-ribopentopyranosyl fluoride | 134110-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3,4-isopropylidene-2-fluoro-2-O-methyl-D-ribopentopyranosyl fluoride
• 英文别名: 2-fluoro-3,4-isopropylidene-2-O-methyl-D-ribo-pento-pyranosyl fluoride；(3aR,7S,7aR)-6,7-difluoro-7-methoxy-2,2-dimethyl-3a,4,6,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran
• CAS: 134110-38-6；134110-42-2；148966-93-2
• 化学式: C₉H₁₄F₂O₄
• 分子量: 224.205
• InChiKey: LBBHZFGRFLXVDK-PQLACBALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  萘酚 、 3,4-isopropylidene-2-fluoro-2-O-methyl-D-ribopentopyranosyl fluoride 在 二氯二茂铪 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 生成 (3aR,5aS,12aR,12bR)-2,2-Dimethyl-12a-(naphthalen-1-yloxy)-3a,5a,12a,12b-tetrahydro-4H-1,3,5,12-tetraoxa-benzo[a]cyclopenta[i]fluorene
  参考文献：
  名称：

  2-Alkoxy-2-fluoro-glycosyl fluorides as 1,2-dielectrophilic synthons for the synthesis of naphtho- and benzo-dihydrofuran derivatives

  摘要：

  Benzo and naphtho-dihydrofuran derivatives were obtained by the reaction of glycosyl fluorides with phenol and naphthol derivatives in the presence of C(p2)MCl(2)/AgOTf (M = Hf Zr). This process include a glycosylation, 1,2-migration and an intramolecular cyclization. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4020(96)00348-1
• 作为产物：
  描述：

  methyl 3,4-O-isopropylidene-β-D-erythro-pentopyranosid-2-ulose 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到3,4-isopropylidene-2-fluoro-2-O-methyl-D-ribopentopyranosyl fluoride
  参考文献：
  名称：

  通过茂金属促进的2-烷氧基-2-氟-糖基氟与苄醇的合成异色烷衍生物

  摘要：

  通过在Cp 2 HfCl 2 / AgClO 4存在下糖基氟化物与苯甲醇反应，通过糖基化，迁移和分子内环化序列，获得了异色烷衍生物。

  DOI：

  10.1016/s0040-4039(00)77614-3

文献信息

• Stereoselective synthesis of nucleosides by metallocene-promoted activation of glycosyl fluorides
  作者：Ma Isabel Matheu、Raouf Echarri、Sergio Catillón

  DOI：10.1016/s0040-4039(00)91869-0

  日期：1992.2

  The Cp2MCl2-AgX (M = Hf, Zr; X = ClO4, OTf) mixture is very effective for the promotion of the coupling of glycosyl fluorides and bis(trimethylsilyl)uracil. The stereoselectivity of the reaction depends on the solvent employed. Application to the synthesis of 1-(3,4 -isopropylidene-2-fluoro-2-O-methyl-alpha-D-ribopentopyranosyl)uracil is described.
• 2-Alkoxy-2-fluoro-glycosyl fluorides as 1,2-dielectrophilic synthons for the synthesis of naphtho- and benzo-dihydrofuran derivatives
  作者：Ma Isable Matheu、Raouf Echarri、Cèlia Domènech、Sergio Castillón

  DOI：10.1016/s0040-4020(96)00348-1

  日期：1996.5

  Benzo and naphtho-dihydrofuran derivatives were obtained by the reaction of glycosyl fluorides with phenol and naphthol derivatives in the presence of C(p2)MCl(2)/AgOTf (M = Hf Zr). This process include a glycosylation, 1,2-migration and an intramolecular cyclization. Copyright (C) 1996 Elsevier Science Ltd
• Synthesis of isochromane derivatives by metallocene-promoted reaction of 2-alkoxy-2-fluoro-glycosyl fluorides with benzyl alcohol
  作者：Ma Isabel Matheu、Raouf Echarri、Sergio Castillón

  DOI：10.1016/s0040-4039(00)77614-3

  日期：1993.4

  Isochromane derivatives have been obtained by reaction of glycosyl fluorides with benzyl alcohol in presence of Cp2HfCl2/ AgClO4, by a glycosylation, migration, and intramolecular cyclization sequence.

  通过在Cp 2 HfCl 2 / AgClO 4存在下糖基氟化物与苯甲醇反应，通过糖基化，迁移和分子内环化序列，获得了异色烷衍生物。