1D-2,4-di-O-benzyl-1-O-p-methoxybenzyl-myo-inositol | 145789-74-8

• 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: 1D-2,4-di-O-benzyl-1-O-p-methoxybenzyl-myo-inositol
• 英文别名: (1R,2R,3S,4R,5R,6S)-6-[(4-methoxyphenyl)methoxy]-3,5-bis(phenylmethoxy)cyclohexane-1,2,4-triol
• CAS: 145789-74-8
• 化学式: C₂₈H₃₂O₇
• 分子量: 480.558
• InChiKey: JIXSXQDMZNHIHN-HKVPEBPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  1D-2,4-di-O-benzyl-1-O-p-methoxybenzyl-myo-inositol 在 四氮唑 、 叔丁基过氧化氢 、 ammonium cerium(IV) nitrate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.0h， 生成 (+/-)-2,6-di-O-benzyl-myo-inositol 1,4,5-tris(dibenzyl phosphate)
  参考文献：
  名称：

  外消旋和对映体纯的肌醇衍生物的制备，用作合成磷脂酰肌醇3-，3,4-双-和3,4,5-三磷酸酯的中间体，以及用于合成1-d-肌醇的类似物1,3,4,5-四磷酸

  摘要：

  摘要这里提供了先前在初步通报中描述的通过1,2-O-异亚丙基-肌醇的锡介导的烯丙基化和苄基化反应获得的产品的详细信息。这些反应的一些产物，特别是3,4,6-三-O-烯丙基-和3,5,6-三-O-烯丙基-1，2-O-异亚丙基-肌醇，已被用于制备中间体，用于合成标题化合物。描述了以下化合物的合成：1l-2,4,5,6-四-O-苄基-1-Op-甲氧基苄基-肌醇（磷脂酰肌醇3-磷酸酯的中间体），1l-2,4,5 -三-O-苄基-肌醇1,6-双（磷酸二苄酯）和1l-2,4,5-三-O-苄基-1,6-二-Op-甲氧基苄基-肌醇（中间体磷脂酰肌醇3,4-二磷酸），1l-2,4-二-O-苄基-肌醇1,5,6-三（磷酸二苄基）和（±）-2,4-二-O-苄基-1 ，5,6-三-对-甲氧基苄基-肌醇（磷脂酰肌醇3,4,5-三磷酸酯的中间体）。在上述制剂中使用的一些中间体也用于合成肌醇衍生物，其适合于制备1d-肌醇1

  DOI：

  10.1016/s0008-6215(96)00211-x
• 作为产物：
  描述：

  (1R,2S,3R,4R,5S,6R)-2,4,5-Tris-allyloxy-3-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexanol 在 三乙烯二胺 、 盐酸 、 RhCl(PPh₃)3 、 sodium hydride 作用下， 反应 7.0h， 生成 1D-2,4-di-O-benzyl-1-O-p-methoxybenzyl-myo-inositol
  参考文献：
  名称：

  Molecular Recognition at the Phosphatidylinositol 3,4,5-Trisphosphate-Binding Site. Studies Using the Permuted Isomers of Phosphatidylinositol Trisphosphate

  摘要：

  Permuted isomers of L-alpha-phosphatidyl-D-myo-inositol trisphosphate (PtdInsP(3)), including PtdIns(3,4,5)P-3, PtdIns(3,4,6)P-3, PtdIns(3,5,6)P-3, and PtdIns(4,5,6)P-3, have been synthesized as part of our effort to understand the underlying principles governing ligand selection for Ptdlns(3,4,5)P-3-specific binding proteins. These PtdInsP(3) isomers are examined by using two PtdIns(3,4,5)P-3-dependent functional assays: binding to the C-terminal SH2 domain of the p85 regulatory subunit of PI 3-kinase and platelet aggregation. Our data show that all these isomers bind to the SH2 domain with comparable affinity despite variation in the regioisomeric distribution of phosphate functions. Moreover, all these phospholipids are capable of triggering platelet aggregation with the relative potency of PtdIns(3,4,5)P-3 > PtdIns(3,5,6)P-3 > PtdIns(4,5,6)P-3 > PtdIns(3,4,6)P-3. Evidence suggests that these PtdInsP(3)'s facilitate cell aggregation by activating Ca2+ influx across the plasma membrane. In contrast, other inositol lipids examined including PtdIns(3,4)P-2, PtdIns(4,5)P-2, PtdIns(3)P, and PtdIns(4)P are ineffective in eliciting the aggregation even at much higher concentrations. Taken together, the present data suggest that the charge density on the phosphorylated inositol ring represents a key factor in determining the phosphoinositide binding specificity of target proteins. It is conceivable that the interaction with the PtdIns(3,4,5)P-3-binding motif requires the participation of all three phosphates on the headgroup of PtdIns(3,4,5)P-3. Consequently, other membrane phosphoinositides (e.g., the bis- and monophosphates) become thermodynamically unfavorable for the binding to these PtdIns(3,4,5)P-3 targets.

  DOI：

  10.1021/jo980356h

文献信息

• The preparation of intermediates for the synthesis of 1d-myo-inositol 1,4,5-trisphosphate, a second messenger for signal transduction in cells
  作者：Trupti Desai、Jill Gigg、Roy Gigg、Sheila Payne、Soledad Penades

  DOI：10.1016/0008-6215(92)85035-x

  日期：1992.10

  Racemic 1,2,4-tri-O-benzyl-5,6-0-isopropylidene-myo-inositol was prepared by a new route involving crotyl (but-2-enyl) ethers and converted into the (-)-omega-camphanates to give the pure crystalline 1L-diastereoisomer and the chirally impure, syrupy ID-diastereoisomer. The latter was converted via the 1-0-allyl or 1-0-p-methoxybenzyl ethers into chirally pure ID-2,3,6-tri-O-benzyl-myo-inositol [required as an intermediate for the synthesis of ID-myo-inositol 1,4,5-trisphosphate (1,4,5-IP3)], which was also prepared by de-p-methoxybenzylation of ID-2,3,6-tri-O-benzyl-1,5-di-0-p-methoxybenzyl-myo-inositol. Racemic 2,4-di-O-benzyl-5,6-0-isopropylidene-1-0-p-methoxybenzyl-myo-inositol was prepared in a similar way to the analogous tribenzyl ether (using crotyl ethers) and the omega-camphanate esters behaved similarly, allowing efficient resolution by crystallisation of the (-)- and (+)-omega-camphanates. Racemic 1,2,4-tri-O-allyl-3-0-(but-2-enyl)-myo-inositol was resolved via the (-)-omega-camphanates and was also converted into 1,2,4-tri-O-(CiS-prop-1-enyl)-myo-inositol, an alternative intermediate for the synthesis of 1,4,5-IP3.