methyl 2,3,4-tri-O-benzyl-6-O-(4-methoxybenzyl)-α-D-glucopyranoside | 142719-06-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-O-(4-methoxybenzyl)-α-D-glucopyranoside
• 英文别名: (2S,3R,4S,5R,6R)-2-methoxy-6-[(4-methoxyphenyl)methoxymethyl]-3,4,5-tris(phenylmethoxy)oxane
• CAS: 142719-06-0
• 化学式: C₃₆H₄₀O₇
• 分子量: 584.709
• InChiKey: OWZUZKXGKZBEKT-GJXDWMKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-O-(4-methoxybenzyl)-α-D-glucopyranoside 在 dicobalt octacarbonyl 、 一氧化碳 、 二甲基苯基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以86%的产率得到甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Co 2（CO）8 -Me 2 PhSiH-CO系统选择性裂解糖的主要对甲氧基苄基保护基的温和有效方法

  摘要：

  提出了一种温和有效的方法，用催化量的Co 2（CO）8，氢硅烷和CO（1 atm）选择性裂解对甲氧基苄基（PMB）醚。裂解反应显示出各种过甲氧基苄基化的糖对伯O- PMB的区域选择性和对O - Bn ，含硫基团和常见的酯保护基的化学选择性。

  DOI：

  10.1016/j.tetlet.2015.07.051
• 作为产物：
  描述：

  4-甲氧基苄醇 在 bismuth(lll) trifluoromethanesulfonate 、 sodium hydride 作用下， 以 二氯甲烷 、 甲苯 、 mineral oil 为溶剂， 反应 3.0h， 生成 methyl 2,3,4-tri-O-benzyl-6-O-(4-methoxybenzyl)-α-D-glucopyranoside
  参考文献：
  名称：

  p-Methoxybenzyl-N-phenyl-2,2,2-trifluoroacetimidate: a versatile reagent for mild acid catalyzed etherification

  摘要：

  PMB-NPTFA la is a new month bench stable and powerful reagent for the formation of PMB ethers. Several alcohols were protected in high yields and short reaction times, using low reagent loading and small catalytic amounts of Bi(OTf)(3). The mild conditions of the reaction confer a good orthogonality to acid- and base-sensitive protecting groups. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.066

文献信息

• A mild and efficient method for the selective cleavage of primary p-methoxybenzyl protecting group of saccharides by Co2(CO)8–Me2PhSiH–CO system
  作者：Peng-zhan Qian、Wang Yao、Lu-bai Huang、Xiang-bao Meng、Zhong-jun Li

  DOI：10.1016/j.tetlet.2015.07.051

  日期：2015.9

  A mild and efficient method to selectively cleave p-methoxybenzyl (PMB) ether with a catalytic amount of Co2(CO)8, hydrosilane and CO (1 atm) is presented. The cleavage reaction shows regioselectivity to primary O-PMB of a variety of permethoxybenzylated saccharides and chemoselectivity to O-Bn, sulfur-containing group and common ester protecting groups.

  提出了一种温和有效的方法，用催化量的Co 2（CO）8，氢硅烷和CO（1 atm）选择性裂解对甲氧基苄基（PMB）醚。裂解反应显示出各种过甲氧基苄基化的糖对伯O- PMB的区域选择性和对O - Bn ，含硫基团和常见的酯保护基的化学选择性。
• Reverse orthogonal strategy for oligosaccharide synthesis
  作者：Kohki Fujikawa、N. Vijaya Ganesh、Yih Horng Tan、Keith J. Stine、Alexei V. Demchenko

  DOI：10.1039/c1cc13409d

  日期：——

  Herein, we report the invention of a novel expeditious concept for oligosaccharide synthesis. Unlike the classic orthogonal strategy based on leaving groups, the reverse approach is based on orthogonal protecting groups, herein p-methoxybenzyl and 4-pentenoyl, which allows for efficient oligosaccharide assembly in the reverse direction.

  在此，我们报告了一种用于寡糖合成的新型快速概念的发明。与基于离去基团的经典正交策略不同，这种反向方法基于正交保护基团，即对甲氧基苄基和 4-戊烯酰基，从而实现了寡糖的高效反向组装。
• Broadening the Scope of the Reverse Orthogonal Strategy for Oligosaccharide Synthesis
  作者：Scott A. Geringer、Gustavo A. Kashiwagi、Alexei V. Demchenko

  DOI：10.1021/acs.joc.2c00905

  日期：2022.8.5

  The reverse orthogonal strategy was invented in 2011 in an attempt to address drawbacks of other strategies for glycan assembly. Different from the classical orthogonal approach that relies on the orthogonality of leaving groups, the reverse strategy is based on orthogonal protecting groups that could be removed during the glycosylation step. This strategy remained largely unexplored due to only one

  反向正交策略于 2011 年发明，试图解决其他聚糖组装策略的缺点。与依赖离去基团正交性的经典正交方法不同，反向策略基于可以在糖基化步骤中去除的正交保护基团。由于只有一种正交保护基团的组合适合这一概念，因此该策略在很大程度上仍未得到探索。本文报道了离去基团和保护基团的新正交组合，有助于简化聚糖组装。还报道了先前报道的反应条件的进一步完善。
• p-Methoxybenzyl-N-phenyl-2,2,2-trifluoroacetimidate: a versatile reagent for mild acid catalyzed etherification
  作者：Nadine Barroca-Aubry、Mohamed Benchekroun、Filipe Gomes、David Bonnaffé

  DOI：10.1016/j.tetlet.2013.07.066

  日期：2013.9

  PMB-NPTFA la is a new month bench stable and powerful reagent for the formation of PMB ethers. Several alcohols were protected in high yields and short reaction times, using low reagent loading and small catalytic amounts of Bi(OTf)(3). The mild conditions of the reaction confer a good orthogonality to acid- and base-sensitive protecting groups. (C) 2013 Elsevier Ltd. All rights reserved.