2,3,4,6-tetra-O-p-chlorobenzyl-β-D-glucopyranosyl phenyl carbonate

• 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: 2,3,4,6-tetra-O-p-chlorobenzyl-β-D-glucopyranosyl phenyl carbonate
• 英文别名: phenyl [(2S,3R,4S,5R,6R)-3,4,5-tris[(4-chlorophenyl)methoxy]-6-[(4-chlorophenyl)methoxymethyl]oxan-2-yl] carbonate
• 化学式: C₄₁H₃₆Cl₄O₈
• 分子量: 798.544
• InChiKey: XBCVZBXIHBDIRO-DTQLOPILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  53
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

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 、 2,3,4,6-tetra-O-p-chlorobenzyl-β-D-glucopyranosyl phenyl carbonate 在 calcium sulfate 、 TrB(C₆F₅)4 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 以93%的产率得到methyl (2,3,4,6-tetra-O-(4-chlorobenzyl)-β-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  使用对氯苄基化糖基碳酸酯作为糖基供体的 1,2-反式糖苷的高立体选择性合成

  摘要：

  2,3,4,6-四-Op-氯苄基-β-D-吡喃葡萄糖基苯基碳酸酯作为一种稳定且易于使用的催化立体选择性合成1,2-反式糖苷的新方法可用的糖基供体。以良好的收率和高立体选择性制备了几种 β-D-吡喃葡萄糖苷。

  DOI：

  10.1246/cl.1998.635

文献信息

• One-Pot Sequential Stereoselective Synthesis of Trisaccharide (Glc<i>β</i>1-6Glc<i>β</i>1-6Glc) by Promotion of Trityl Tetrakis(pentafluorophenyl)borate Catalyst
  作者：Teruaki Mukaiyama、Yoshinari Wakiyama、Kazuo Miyazaki、Kazuya Takeuchi

  DOI：10.1246/cl.1999.933

  日期：1999.9

  A one-pot synthesis of trisaccharides was successfully carried out by combination of two types of the trityl tetrakis(pentafluorophenyl)borate catalyzed stereoselective glycosylation reactions. Selective activation of a glycosyl phenyl carbonate in the presence of a thioglycoside allows two successive glycosyl coupling in one-pot manner to afford several protected trisaccharides, Glcβ1-6Glcβ1-6Glc, in good to high yields.

  通过结合两种类型的三苯基四氟苯基硼酸盐催化的立体选择性糖苷化反应，成功实现了一锅法合成三糖。在硫糖苷存在的情况下，选择性激活糖苷苯基碳酸酯允许在一锅中进行两次连续的糖苷偶联，获得了几种保护的三糖Glcβ1-6Glcβ1-6Glc，产率为中高等。
• The Trityl Tetrakis(pentafluorophenyl)borate Catalyzed Stereoselective Glycosylation Using New Glycosyldonor, 3,4,6-Tri-<i>O</i>-benzyl-2-<i>O</i>-<i>p</i>-toluoyl-β-D-glucopyranosyl Phenylcarbonate
  作者：Kazuya Takeuchi、Takayuki Tamura、Teruaki Mukaiyama

  DOI：10.1246/cl.2000.122

  日期：2000.2

  The trityl tetrakis(pentafluorophenyl)borate [TrB(C6F5)4] catalyzed stereoselective synthesis of various disaccharides was successfully carried out by treating a new 2-O-acyl-protected glycosyl donor, 3,4,6-tri-O-benzyl-2-O-p-toluoyl-β-D-glucopyranosyl phenylcarbonate, with several glycosyl acceptors, thioglycosides, affording the corresponding disaccharides in high yields.

  三苯基四氟苯酯 [TrB(C6F5)4] 催化的各种二糖的立体选择性合成成功地通过处理一种新的 2-O-酰基保护的糖苷供体 3,4,6-三-O-苄基-2-O-对甲苯酰基-β-D-葡萄糖噻吩碳酸酯与几种糖苷接受体硫糖苷进行，实现了高产率的相应二糖的合成。
• Highly Stereoselective Synthesis of 1,2-trans-Glycosides Using p-Chlorobenzylated Glycosyl Carbonate as Glycosyl Donor
  作者：Teruaki Mukaiyama、Kazuo Miyazaki、Hiromi Uchiro

  DOI：10.1246/cl.1998.635

  日期：1998.7

  A new and efficient method for catalytic stereoselective synthesis of 1,2-trans-glycosides was successfully established by use of 2,3,4,6-tetra-O-p-chlorobenzyl-β-D-glucopyranosyl phenyl carbonate as a stable and easily-available glycosyl donor. Several β-D-glucopyranosides were prepared in good yields with high stereoselectivities.

  2,3,4,6-四-Op-氯苄基-β-D-吡喃葡萄糖基苯基碳酸酯作为一种稳定且易于使用的催化立体选择性合成1,2-反式糖苷的新方法可用的糖基供体。以良好的收率和高立体选择性制备了几种 β-D-吡喃葡萄糖苷。