2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl fluoride | 304453-54-1

• 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-galactopyranosyl fluoride
• 英文别名: [(2S,3R,4S,5S,6R)-2-fluoro-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
• CAS: 304453-54-1
• 化学式: C₃₄H₃₃FO₆
• 分子量: 556.631
• InChiKey: GWVXVDXONKINSS-MRRLEEDCSA-N

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-galactopyranosyl fluoride 在 calcium sulfate 、 三氟甲磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.5h， 以93%的产率得到methyl 6-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  A Catalytic and Stereoselective Glycosylation withβ-Glycosyl Fluorides

  摘要：

  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).

  DOI：

  10.1002/1522-2675(20000809)83:8<1901::aid-hlca1901>3.0.co;2-q
• 作为产物：
  描述：

  ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以61.8%的产率得到2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl fluoride
  参考文献：
  名称：

  A Catalytic and Stereoselective Glycosylation withβ-Glycosyl Fluorides

  摘要：

  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).

  DOI：

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

文献信息

• Efficient synthesis of core 2 class glycosyl amino acids by one-pot glycosylation approach
  作者：Hiroshi Tanaka、Masaatsu Adachi、Takashi Takahashi

  DOI：10.1016/j.tetlet.2003.12.042

  日期：2004.2

  We describe the one-pot synthesis of core 2 class branched oligosaccharides initiated by chemo-selective glycosylation of silyl anther. Glycosylation of 6-O-silyl-4-benzyl-2-azido-thiogalactoside with glycosyl fluoride provided selectively 6-glycosylated thioglycoside without both O-glycosylation at the 3 position and S-glycosylation. Subsequent coupling of galactosyl fluoride and amino acids afforded the protected branched oligosaccharides in good yields. (C) 2003 Elsevier Ltd. All rights reserved.
• 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).