2'-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride | 149625-91-2

• 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: 2'-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride
• 英文别名: 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride；[(2S,3R,4S,5R,6R)-2-fluoro-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
• CAS: 149625-91-2
• 化学式: C₃₄H₃₃FO₆
• 分子量: 556.631
• InChiKey: GWVXVDXONKINSS-IZDBAANZSA-N

物化性质

• 沸点：
  654.6±55.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 2'-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride 在 calcium sulfate 、 三氟甲磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 以97.1%的产率得到methyl O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Trifluoromethanesulfonic Acid (TfOH)-Catalyzed Stereoselective Glycosylation Using Glycosyl Fluoride

  摘要：

  利用催化量的三氟甲磺酸（TfOH），成功地将 2-O-苯甲酰基-3,4,6-三-O-苄基-β-d-葡糖基氟化物 6 与多种糖基受体进行了立体选择性糖基化。

  DOI：

  10.1246/cl.2000.696
• 作为产物：
  描述：

  (3R,4R,5S)-4,5-Bis-benzyloxy-3-benzyloxymethyl-2,7-dioxa-bicyclo[4.1.0]heptane 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 2'-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride
  参考文献：
  名称：

  Application of the glycal assembly strategy to the synthesis of a branched oligosaccharide: the first synthesis of a complex saponin

  摘要：

  DOI：

  10.1021/ja00071a077

文献信息

• Trifluoromethanesulfonic Acid (TfOH)-Catalyzed Stereoselective Glycosylation Using Glycosyl Fluoride
  作者：Teruaki Mukaiyama、Hideki Jona、Kazuya Takeuchi

  DOI：10.1246/cl.2000.696

  日期：2000.6

  Stereoselective glycosylation of 2-O-benzoyl-3,4,6-tri-O-benzyl-β-d-glucosyl fluoride 6 with several glycosyl acceptors is successfully carried out by using a catalytic amount of trifluoromethanesulfonic acid (TfOH).

  利用催化量的三氟甲磺酸（TfOH），成功地将 2-O-苯甲酰基-3,4,6-三-O-苄基-β-d-葡糖基氟化物 6 与多种糖基受体进行了立体选择性糖基化。
• First Synthesis of a Digitalis Saponin. Demonstration of the Scope and Limitations of a Convergent Scheme for Branched Oligosaccharide Synthesis by the Logic of Glycal Assembly
  作者：John T. Randolph、Samuel J. Danishefsky

  DOI：10.1021/ja00126a010

  日期：1995.5

  The synthesis of complex glycosides, with branching at C-2, is demonstrated. The key element involves the use of a 1,2-oxirane donor. Upon glycosylation, a C-2 hydroxyl is exposed to serve as the acceptor in the next glycosylation. Branching at C-2 with a beta-linked glycoside at C-1 was not achievable with epoxy 23 donor, but was accomplished with fluoro donor 25, in turn derived from 23. (See 19 + 18 --> 20; 20 + 25 --> 26. Compound 26 was deprotected to complete the first total synthesis of a natural saponin, desgalactotigonin (3)). A limitation in stereospecifity in the use of donor 23 and monoprotected galactal acceptor 28 was also encountered.
• Application of the glycal assembly strategy to the synthesis of a branched oligosaccharide: the first synthesis of a complex saponin
  作者：John T. Randolph、Samuel J. Danishefsky

  DOI：10.1021/ja00071a077

  日期：1993.9
• A Catalytic and Stereoselective Glycosylation withβ-Glycosyl Fluorides
  作者：Teruaki Mukaiyama、Kazuya Takeuchi、Hideki Jona、Hisashi Maeshima、Terunobu Saitoh

  DOI：10.1002/1522-2675(20000809)83:8<1901::aid-hlca1901>3.0.co;2-q

  日期：2000.8.9

  A catalytic and stereoselective glycosylation of several glycosyl accepters with beta-D-glycosyl fluoride was successfully performed in the presence of a catalytic amount of trityl tetrakis(pentafluorophenyl)borate (TrB(C6F5)(4)) or trifluoromethanesulfonic acid (TfOH). When TrB(C6F5)(4) was used as a catalyst in the solvent pivalonitrile/(trifluoromethyl)benzene 1:5, the glycosylation proceeded smoothly to afford the glycosides in high yields with high beta-D-stereoselectivities (see Table 3). Further, the glycosylation by the armed-disarmed strategy in the presence of this catalyst was established (see Table 4). Similarly, glycosylation catalyzed by the strong protic acid TfOH afforded the corresponding beta-D-glycosides in good-to-excellent yields on treating beta-D-glycosyl fluorides having a 2-O-benzoyl group with various glycosyl accepters including thioglycosides (see Tables 6 and 7).