Acetic acid (1S,2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-hydroxy-cyclohexyl ester | 214068-40-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Acetic acid (1S,2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-hydroxy-cyclohexyl ester
• CAS: 214068-40-3
• 化学式: C₃₈H₄₂O₉
• 分子量: 642.746
• InChiKey: IZWKMLMTIBJPFO-XUCWYYSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  47.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  101.91
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-hydroxy-cyclohexyl ester 在 四氮唑 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 反应 2.75h， 生成 Phosphoric acid dibenzyl ester (1R,2S,3S,4R,5S,6R)-2,6-bis-benzyloxy-3,5-bis-benzyloxymethoxy-4-hydroxy-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)-4,6-O-benzylidene-α-D-glucopyranoside 在 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 、 对甲苯磺酸 、 三乙胺 、 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 (1S,2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-hydroxy-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