methyl 2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-α-D-glucopyranoside | 1338712-08-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-α-D-glucopyranoside
• 英文别名: methyl 2,3,6-tri-O-benzyl-4-O-p-methoxybenzyl-α-D-glucopyranoside；Bn(-2)[Bn(-3)][Mob(-4)][Bn(-6)]a-Glc1Me；(2S,3R,4S,5R,6R)-2-methoxy-5-[(4-methoxyphenyl)methoxy]-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 1338712-08-5
• 化学式: C₃₆H₄₀O₇
• 分子量: 584.709
• InChiKey: VJKNJMQMGFSUML-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 2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-α-D-glucopyranoside 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.04h， 以96%的产率得到甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Chemoselective Cleavage of p-Methoxybenzyl and 2-Naphthylmethyl Ethers Using a Catalytic Amount of HCl in Hexafluoro-2-propanol

  摘要：

  A new, fast, mild and chemoselective deprotection method to cleave p-methoxybenzyl and 2-naphthylmethyl ethers using catalytic amounts of hydrochloric acid in a 1:1 mixture of hexafluoro-2-propanol (HFIP) and methylene chloride (DCM) is described. The scope of the methodology becomes apparent from 14 examples of orthogonally protected monosaccharides that are subjected to HCl/HFIP treatment. The applicability of the HCl/HFIP method is illustrated by the synthesis of a sulfated beta-mannuronic acid disaccharide.

  DOI：

  10.1021/acs.joc.5b01030
• 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 2.0h， 生成 methyl 2,3,6-tri-O-benzyl-4-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

• 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。