methyl 2,3,4-tri-O-(p-methoxyphenylmethyl)-6-O-trimethylphenyl-1-α-D-glucopyranoside | 137897-37-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: methyl 2,3,4-tri-O-(p-methoxyphenylmethyl)-6-O-trimethylphenyl-1-α-D-glucopyranoside
• 英文别名: (2S,3R,4S,5R,6R)-2-methoxy-3,4,5-tris[(4-methoxyphenyl)methoxy]-6-(trityloxymethyl)oxane
• CAS: 137897-37-1
• 化学式: C₅₀H₅₂O₉
• 分子量: 796.957
• InChiKey: NLTBVBGKPSLWKQ-AGCKAGJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.15
• 重原子数：
  59.0
• 可旋转键数：
  19.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  83.07
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-(p-methoxyphenylmethyl)-6-O-trimethylphenyl-1-α-D-glucopyranoside 在 甲醇 、 草酰氯 、 硫酸 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3S,4S,5R,6S)-6-Methoxy-3,4,5-tris-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde
  参考文献：
  名称：

  A Stereoselective method to (E)- and (Z)-fluorovinyl phosphonates Utilizing Palladium(0) coupling methodology

  摘要：

  The first stereoselective method to both (E)- and (Z)-fluorovinyl phosphonates from fluorovinyl iodides was developed utilizing a palladium(0) based coupling protocol. This method allowed the preparation of (E)- and (Z)-fluorovinyl phosphonic acid analogs of glucose-6-phosphate that were designed to be mechanism-based inhibitors of inositol synthase.

  DOI：

  10.1016/s0040-4039(00)79286-0
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 吡啶 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2,3,4-tri-O-(p-methoxyphenylmethyl)-6-O-trimethylphenyl-1-α-D-glucopyranoside
  参考文献：
  名称：

  A Stereoselective method to (E)- and (Z)-fluorovinyl phosphonates Utilizing Palladium(0) coupling methodology

  摘要：

  The first stereoselective method to both (E)- and (Z)-fluorovinyl phosphonates from fluorovinyl iodides was developed utilizing a palladium(0) based coupling protocol. This method allowed the preparation of (E)- and (Z)-fluorovinyl phosphonic acid analogs of glucose-6-phosphate that were designed to be mechanism-based inhibitors of inositol synthase.

  DOI：

  10.1016/s0040-4039(00)79286-0

文献信息

• Chiral acidic amino acids as tethers for intramolecular glycosylation
  作者：Katsuya Fukushima、Takashi Kikuma、Yoichi Takeda

  DOI：10.1080/07328303.2021.2015364

  日期：2021.7.24

  Abstract Intramolecular glycosylation with peptides as tethers is attractive for the synthesis of oligosaccharides because conjugation between the amino acids present in the tethers is facile. However, few studies have been published about the effects of the amino acid side chain length and amino acid chirality on the glycosylation process. In this study, we revealed that the chain length of the amino

  摘要 以肽作为系链的分子内糖基化对于寡糖的合成具有吸引力，因为存在于系链中的氨基酸之间的缀合是容易的。然而，很少有关于氨基酸侧链长度和氨基酸手性对糖基化过程的影响的研究发表。在这项研究中，我们发现氨基酸的链长可以调节糖基化过程的区域选择性，这是基于我们观察到当系链是具有彼此连接的天冬氨酸残基的那些时，优选 1,2 连接的产物，而对于基于谷氨酸的系链，1,3-连接的产品是优选的。然而，发现氨基酸手性对糖基化反应的产率和立体选择性没有影响。
• Chemoselective deprotection of acid labile primary hydroxyl protecting groups under CBr4-photoirradiation conditions
  作者：Ming-Yi Chen、Laxmikant N. Patkar、Kuo-Cheng Lu、Adam Shih-Yuan Lee、Chun-Cheng Lin

  DOI：10.1016/j.tet.2004.09.095

  日期：2004.12

  The CBr4-photoirradiation in methanol generates a controlled source of HBr, which can chemoselectively deprotect commonly used hydroxyl-protecting groups in saccharides and nucleosides, such as tert-butyldimethylsilyl, isopropylidene, benzylidene and triphenyl ethers in the presence of other acid-labile functional groups. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of enantiomerically pure, P-1-tethered inositol tetrakis(phosphate) affinity labels via a Ferrier rearrangement
  作者：Virginia A. Estevez、Glenn D. Prestwich

  DOI：10.1021/ja00026a043

  日期：1991.12