(2S,3S,4S,5R,6S)-3,5-Bis-benzyloxy-6-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde | 194207-24-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6S)-3,5-Bis-benzyloxy-6-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde
• 英文别名: (2S,3S,4S,5R,6S)-6-methoxy-4-[(4-methoxyphenyl)methoxy]-3,5-bis(phenylmethoxy)oxane-2-carbaldehyde
• CAS: 194207-24-4
• 化学式: C₂₉H₃₂O₇
• 分子量: 492.569
• InChiKey: AQAYXAPDCVGWPG-RQKPWJHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6S)-3,5-Bis-benzyloxy-6-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde 在 四氮唑 、 Proton Sponge 、 mercury(II) diacetate 、 四丁基溴化铵 、 三乙酰氧基硼氢化钠 、 potassium carbonate 、 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 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 30.5h， 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 草酰氯 、 硫酸 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 3.0h， 生成 (2S,3S,4S,5R,6S)-3,5-Bis-benzyloxy-6-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde
  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

文献信息

• 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.