3,4-di-O-benzoyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride | 304453-34-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-di-O-benzoyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride
• 英文别名: [(2R,3S,4R,5R,6S)-4-benzoyloxy-5-(5,6-dichloro-1,3-dioxoisoindol-2-yl)-6-fluoro-2-(hydroxymethyl)oxan-3-yl] benzoate
• CAS: 304453-34-7
• 化学式: C₂₈H₂₀Cl₂FNO₈
• 分子量: 588.373
• InChiKey: WVHYGSUQQFCJHR-MRKXFKPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4,6-四-O-苄基-β-D-吡喃葡萄糖酰氟 、 3,4-di-O-benzoyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride 在 hydrogen tetrakis(pentafluorophenyl)borate 、 5A molecular sieve 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 3.0h， 生成 3,4-di-O-benzoyl-6-O-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride 、 3,4-di-O-benzoyl-6-O-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride
  参考文献：
  名称：

  使用糖基氟化物的质子酸催化立体选择性糖基化

  摘要：

  在 MS 5A 存在下，使用各种质子酸成功地进行了各种糖基受体（如甲基糖苷、硫糖苷或脱臂糖基氟）与苄基保护的武装糖基氟的催化和立体选择性糖基化。在三氟甲磺酸 (TfOH) 或高氯酸 (HClO4) 用于乙醚 (Et2O) 的情况下，主要产物为 α-糖苷，而当四（五氟苯基）硼酸 [HB(C6F5) )4] 用于三氟甲基苯 (BTF)-新戊腈 (tBuCN) = 5:1 的混合溶剂中。这种糖基化的立体选择性受催化剂抗衡阴离子的性质以及溶剂的性质控制。还，

  DOI：

  10.1246/bcsj.75.291
• 作为产物：
  描述：

  1-acetoxy-3,4,6-tri-O-acetyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranoside 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 二乙胺基三氟化硫 、 三氟化硼乙醚 、 氢氟酸 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 47.17h， 生成 3,4-di-O-benzoyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl 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

• 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).
• Protic Acid Catalyzed Stereoselective Glycosylation Using Glycosyl Fluorides
  作者：Hideki Jona、Hiroki Mandai、Warinthorn Chavasiri、Kazuya Takeuchi、Teruaki Mukaiyama

  DOI：10.1246/bcsj.75.291

  日期：2002.2

  A catalytic and stereoselective glycosylation of various glycosyl acceptors, such as methyl glycosides, thioglycosides, or a disarmed glycosyl fluoride, with benzyl-protected armed glycosyl fluoride was successfully carried out by using various protic acids in the presence of MS 5A. In the cases when trifluoromethanesulfonic acid (TfOH) or perchloric acid (HClO4) was used in diethyl ether (Et2O), α-glycosides

  在 MS 5A 存在下，使用各种质子酸成功地进行了各种糖基受体（如甲基糖苷、硫糖苷或脱臂糖基氟）与苄基保护的武装糖基氟的催化和立体选择性糖基化。在三氟甲磺酸 (TfOH) 或高氯酸 (HClO4) 用于乙醚 (Et2O) 的情况下，主要产物为 α-糖苷，而当四（五氟苯基）硼酸 [HB(C6F5) )4] 用于三氟甲基苯 (BTF)-新戊腈 (tBuCN) = 5:1 的混合溶剂中。这种糖基化的立体选择性受催化剂抗衡阴离子的性质以及溶剂的性质控制。还，