methyl 3-O-(p-methoxybenzyl)-α-D-glucopyranoside | 214068-15-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-(p-methoxybenzyl)-α-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-methoxy-4-[(4-methoxyphenyl)methoxy]oxane-3,5-diol
• CAS: 214068-15-2
• 化学式: C₁₅H₂₂O₇
• 分子量: 314.335
• InChiKey: ILQZXHKKGJJBBG-ZSAUSMIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  97.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-O-(p-methoxybenzyl)-α-D-glucopyranoside 在 四氮唑 、 4-二甲氨基吡啶 、 草酰氯 、 Proton Sponge 、 硫酸 、 mercury(II) diacetate 、 四丁基溴化铵 、 三乙酰氧基硼氢化钠 、 sodium hydride 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium chloride 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 33.5h， 生成 Acetic acid (1R,2R,3S,4R,5R,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester
  参考文献：
  名称：

  Asymmetric Total Synthesis of Phosphatidylinositol 3-Phosphate and 4-Phosphate Derivatives

  摘要：

  New asymmetric syntheses of phosphatidylinositol 3-phosphate (PtdIns(3)P) and phosphatidylinositol 4-phosphate (PtdIns(4)P) derivatives are described. Key intermediates were used to prepare diacylglyceryl moieties with dibutyryl, dioctanoyl, and dihexadecanoyl chains. In addition, a modified route provided PtdIns(3)P and PtdIns(4)P triesters with P-1-linked aminopropyl groups for preparation of affinity probes. The synthesis of the inosityl precursor employed a dibutyltin oxide-mediated p-methoxybenzyl (PMB) etherification to give either the 2-PMB- or the 3-PMB-protected glucopyranosides. The Ferrier rearrangement was used to convert suitably protected glucose derivatives to enantiomerically pure, differentially protected D-myo-inositol key intermediates. A versatile phosphoramidite reagent was employed to allow synthesis of PtdInsP(n), derivatives with diacylglyceryl moieties of different chain lengths.

  DOI：

  10.1021/jo980501r
• 作为产物：
  描述：

  methyl 3-O-(p-methoxybenzyl)-6-O-trityl-α-D-glucopyranoside 在 四溴化碳 作用下， 以 甲醇 为溶剂， 反应 38.0h， 以91%的产率得到methyl 3-O-(p-methoxybenzyl)-α-D-glucopyranoside
  参考文献：
  名称：

  CBr4-photoirradiation protocol for chemoselective deprotection of acid labile primary hydroxyl protecting groups

  摘要：

  CBr4-photoirradiation protocol was found to be a mild, highly efficient and selective method for deprotection of isopropylidene, benzylidene, triphenylmethyl and tert-butyldimethylsilyl protecting groups on sugar molecules. The conditions of this reaction can also be used to cleave peptides off from acid-labile resin linkers in solid-phase peptide synthesis. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.205

文献信息

• CBr4-photoirradiation protocol for chemoselective deprotection of acid labile primary hydroxyl protecting groups
  作者：Ming-Yi Chen、Laxmikant N. Patkar、Mi-Dan Jan、Adam Shih-Yuan Lee、Chun-Cheng Lin

  DOI：10.1016/j.tetlet.2003.10.205

  日期：2004.1

  CBr4-photoirradiation protocol was found to be a mild, highly efficient and selective method for deprotection of isopropylidene, benzylidene, triphenylmethyl and tert-butyldimethylsilyl protecting groups on sugar molecules. The conditions of this reaction can also be used to cleave peptides off from acid-labile resin linkers in solid-phase peptide synthesis. (C) 2003 Elsevier Ltd. All rights reserved.
• Asymmetric Total Synthesis of Phosphatidylinositol 3-Phosphate and 4-Phosphate Derivatives
  作者：Jian Chen、Li Feng、Glenn D. Prestwich

  DOI：10.1021/jo980501r

  日期：1998.9.1

  New asymmetric syntheses of phosphatidylinositol 3-phosphate (PtdIns(3)P) and phosphatidylinositol 4-phosphate (PtdIns(4)P) derivatives are described. Key intermediates were used to prepare diacylglyceryl moieties with dibutyryl, dioctanoyl, and dihexadecanoyl chains. In addition, a modified route provided PtdIns(3)P and PtdIns(4)P triesters with P-1-linked aminopropyl groups for preparation of affinity probes. The synthesis of the inosityl precursor employed a dibutyltin oxide-mediated p-methoxybenzyl (PMB) etherification to give either the 2-PMB- or the 3-PMB-protected glucopyranosides. The Ferrier rearrangement was used to convert suitably protected glucose derivatives to enantiomerically pure, differentially protected D-myo-inositol key intermediates. A versatile phosphoramidite reagent was employed to allow synthesis of PtdInsP(n), derivatives with diacylglyceryl moieties of different chain lengths.