2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl)-α-D-glucopyranosiden

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl)-α-D-glucopyranosiden
• 英文别名: methyl 6-β-(2,3,4,6-tetra-O-pivaloylglucopyranosyl)-2,3,4-tri-O-benzyl-α-glucopyranoside；Methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl)-α-D-galactopyranoside；methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl)-α-D-glucopyranoside；pivaloyl(-2)[pivaloyl(-3)][pivaloyl(-4)][pivaloyl(-6)]Glc(b1-6)[Bn(-2)][Bn(-3)][Bn(-4)]a-Glc1Me；[(2R,3R,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]oxan-2-yl]methyl 2,2-dimethylpropanoate
• 化学式: C₅₄H₇₄O₁₅
• 分子量: 963.173
• InChiKey: SEEYOVZCJQWVAV-GHRDNTFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  69
• 可旋转键数：
  26
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  2,3,4,6-O-四特戊酰基-alpha-D-溴代吡喃葡萄糖 在 4 A molecular sieve 、 lithium perchlorate 、 silver fluoride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 40.0h， 生成 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl)-α-D-glucopyranosiden
  参考文献：
  名称：

  Boehm, Gerd; Waldmann, Herbert, Liebigs Annalen, 1996, # 4, p. 621 - 626

  摘要：

  DOI：

文献信息

• A Highly Stereoselective Synthesis of β-Glucosides from Pentaacylglucopyranose and Alkyl Silyl Ether by the Use of a Catalytic Amount of Active Species Generated from Methyltrichlorosilane and Silver Perchlorate
  作者：Teruaki Mukaiyama、Manabu Katsurada、Yousuke Iida

  DOI：10.1246/cl.1992.2105

  日期：1992.11

  An efficient catalytic β-glycosylation reaction starting from pentaacylglucopyranose and alkyl silyl ether was performed using an active species generated from MeSiCl3 and AgClO4. 1-O-Acetyl-2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranose stereoselectively reacted with alkyl silyl ethers with the assistance of neighboring effect to give the corresponding β-glucosides in high yields.

  利用由 MeSiCl3 和 AgClO4 生成的活性物质，从五乙酰吡喃葡萄糖和烷基硅基醚开始，进行了高效的 β-糖基化催化反应。在邻位效应的帮助下，1-O-乙酰基-2,3,4,6-四-O-特戊酰基-β-D-吡喃葡萄糖与烷基硅醚发生了立体选择性反应，以高产率得到了相应的β-葡糖苷。
• Catalytic Decarboxylative Glycosylation Promoted by Hafnium(IV) ­Trifluoromethanesulfonate: β-Selective Glycosylation via a Mixed Carbonate of an Acyl-Protected Donor Sugar
  作者：Shiro Ikegami、Isao Azumaya、Masaomi Kotani

  DOI：10.1055/s-2004-822885

  日期：——

  Acyl-protected mixed carbonates were effectively decarboxylated by catalytic amounts (2-5 mol%) of hafnium(IV) trifluoromethanesulfonate in dichloromethane at room temperature to give the corresponding β-glycosides in excellent yields.

  酰基保护的混合碳酸酯在室温下通过催化量（2-5 mol%）的三氟甲磺酸铪（IV）在二氯甲烷中有效脱羧，以优异的产率得到相应的β-糖苷。
• An efficient synthesis of mixed β-carbonates of acyl-protected sugar and their decarboxylative glycosidation promoted by trimethylsilyl trifluoromethanesulfonate
  作者：Isao Azumaya、Toshihiro Niwa、Masaomi Kotani、Takamasa Iimori、Shiro Ikegami

  DOI：10.1016/s0040-4039(99)00843-6

  日期：1999.6

  Mixed beta-carbonates of acyl-protected sugar are stereoselectively prepared by using an N-succinimidyl group for activation of the acceptor alcohol carbonate. The glycosyl carbonates are smoothly decarboxylated by trimethylsilyl trifluoromethanesulfonate (Me3SiOTf) to give beta-glycosides preferentially in high yields. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 2-Pyridyl glycoside: an alternative glycosyl donor in preactivation protocol
  作者：De-Cai Xiong、An-Qi Yang、Yang Yu、Xin-Shan Ye

  DOI：10.1016/j.tetlet.2014.11.066

  日期：2015.1

  2-Pyridyl glycosides have been identified to be powerful glycosyl donors for the preactivation-based oligosaccharide synthesis. By using stoichiometric amount of Tf2O, the 2-pyridyl glycosides were pre-activated, which subsequently underwent glycosylation reactions smoothly to produce the coupled products in high yields. Furthermore, the 2-pyridyl glycosides were applied to the efficient oligosaccharide assembly by the preactivation-based one-pot oligosaccharide synthesis protocol. (C) 2014 Elsevier Ltd. All rights reserved.
• Boehm, Gerd; Waldmann, Herbert, Liebigs Annalen, 1996, # 4, p. 621 - 626
  作者：Boehm, Gerd、Waldmann, Herbert

  DOI：——

  日期：——