Phosphoric acid benzyl ester (1S,2R,3S,4S,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(4-methoxy-benzyloxy)-cyclohexyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester | 1054657-08-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phosphoric acid benzyl ester (1S,2R,3S,4S,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(4-methoxy-benzyloxy)-cyclohexyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
• 英文别名: benzyl [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl [(1S,2R,3R,4S,5S,6R)-3-[(4-methoxyphenyl)methoxy]-4,5-bis(phenylmethoxy)-2,6-bis(phenylmethoxymethoxy)cyclohexyl] phosphate
• CAS: 1054657-08-7
• 化学式: C₅₇H₆₅O₁₄P
• 分子量: 1005.11
• InChiKey: BGLKYQRASBXEJY-VAWNHJJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  72
• 可旋转键数：
  28
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  Phosphoric acid benzyl ester (1S,2R,3S,4S,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(4-methoxy-benzyloxy)-cyclohexyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 在 四氮唑 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.5h， 生成 Phosphoric acid benzyl ester (1S,2R,3S,4S,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester (S)-2,3-dihydroxy-propyl 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 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-D-glucopyranoside 在 四氮唑 、 sodium hydroxide 、 草酰氯 、 Proton Sponge 、 mercury(II) diacetate 、 四丁基溴化铵 、 三乙酰氧基硼氢化钠 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 、 sodium chloride 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 二甲基亚砜 、 乙腈 为溶剂， 反应 29.0h， 生成 Phosphoric acid benzyl ester (1S,2R,3S,4S,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(4-methoxy-benzyloxy)-cyclohexyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl 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