ethyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside | 143995-75-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Gal(b1-6)[Bz(-2)][Bz(-3)][Bz(-4)]Glc(b)-SEt；[(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-ethylsulfanyloxan-2-yl]methoxy]oxan-2-yl]methyl benzoate
• CAS: 143995-75-9
• 化学式: C₆₃H₅₄O₁₇S
• 分子量: 1115.18
• InChiKey: ICOPVIPFFPCYJO-OITHESAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  81
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  237
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  ethyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside 、 4,5-dihydrothiazol-2-yl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside 在 DMTST 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以64%的产率得到2-thiazolinyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  On Orthogonal and Selective Activation of Glycosyl Thioimidates and Thioglycosides: Application to Oligosaccharide Assembly

  摘要：

  Discrimination among S-thiazolinyl (STaz), S-benzoxazolyl (SBox), and S-ethyl anomeric leaving groups was achieved by fine-tuning activation conditions. Preferential glycosidation of a certain leaving group is determined neither by the strength of the activating reagent nor by the stability of the leaving group itself; instead, the type of activation plays the key role. The activation conditions established herein were applied to a sequential five-step synthesis of a hexasaccharide using six monosaccharide building blocks equipped with six different leaving groups.

  DOI：

  10.1021/jo201117s
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 三氟甲磺酸 吡啶 、 N-碘代丁二酰亚胺 、 三氟化硼乙醚 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 0.03h， 生成 ethyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  碘离子介导的苯基硒代糖苷的糖苷化

  摘要：

  完全苄基化或苯甲酰化的苯基硒代糖苷可以通过促进剂碘鎓二对称-可力丁高氯酸盐（IDCP）或N-碘代琥珀酰亚胺和催化三氟甲磺酸（NIS / TfOH目录）来活化。在1,2-顺-或1,2-反式连接的二糖的化学选择性合成中说明了碘硒离子介导的苯基硒代糖苷的糖苷化潜力。

  DOI：

  10.1002/recl.19921110706

文献信息

• Glycosyl thioimidates in a highly convergent one-pot strategy for oligosaccharide synthesis
  作者：Papapida Pornsuriyasak、Alexei V. Demchenko

  DOI：10.1016/j.tetasy.2004.11.029

  日期：2005.1

  Application of two classes of thioimidoyl derivatives, S-benzoxazolyl (SBox) and S-thiazolyl (STaz) glycosides to selective activation over thioglycosides is described. These results allowed us to synthesize a tetrasaccharide derivative using a leaving group differentiated one-pot strategy in 73% yield over three sequential glycosylation steps. (C) 2004 Elsevier Ltd. All rights reserved.
• Iodonium ion-mediated glycosidations of phenyl selenoglycosides
  作者：H. M. Zuurmond、P. A. M. van der Klein、P. H. van der Meer、G. A. van der Marel、J. H. van Boom

  DOI：10.1002/recl.19921110706

  日期：——

  Fully benzylated or benzoylated phenyl selenoglycosides can be activated by the promoters iodonium di-sym-collidine perchlorate (IDCP) or N-iodosuccinimide and catalytic triflic acid (NIS/TfOH cat.). The potential of the iodonium ion-mediated glycosidations of phenyl selenoglycosides is illustrated in the chemoselective synthesis of 1,2-cis-or 1,2-trans-linked disaccharides.

  完全苄基化或苯甲酰化的苯基硒代糖苷可以通过促进剂碘鎓二对称-可力丁高氯酸盐（IDCP）或N-碘代琥珀酰亚胺和催化三氟甲磺酸（NIS / TfOH目录）来活化。在1,2-顺-或1,2-反式连接的二糖的化学选择性合成中说明了碘硒离子介导的苯基硒代糖苷的糖苷化潜力。
• On Orthogonal and Selective Activation of Glycosyl Thioimidates and Thioglycosides: Application to Oligosaccharide Assembly
  作者：Sophon Kaeothip、Alexei V. Demchenko

  DOI：10.1021/jo201117s

  日期：2011.9.16

  Discrimination among S-thiazolinyl (STaz), S-benzoxazolyl (SBox), and S-ethyl anomeric leaving groups was achieved by fine-tuning activation conditions. Preferential glycosidation of a certain leaving group is determined neither by the strength of the activating reagent nor by the stability of the leaving group itself; instead, the type of activation plays the key role. The activation conditions established herein were applied to a sequential five-step synthesis of a hexasaccharide using six monosaccharide building blocks equipped with six different leaving groups.