1,2-di-O-hexadacanoyl-sn-glycerobenzyl (N,N-diisopropylamino)phopshoramidite | 120595-85-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1,2-di-O-hexadacanoyl-sn-glycerobenzyl (N,N-diisopropylamino)phopshoramidite
• 英文别名: 1,2-di-O-hexadecanoyl-sn-glycerobenzyl (N,N-diisopropylamino)phosphoramidite；1,2-di-O-palmitoyl-sn-glycerol 3-(benzyl N,N-diisopropylphosphoramidite)；[(2S)-3-[[di(propan-2-yl)amino]-phenylmethoxyphosphanyl]oxy-2-hexadecanoyloxypropyl] hexadecanoate
• CAS: 120595-85-9
• 化学式: C₄₈H₈₈NO₆P
• 分子量: 806.204
• InChiKey: KEIYZCAVVCVQIB-WOUDJOTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.9
• 重原子数：
  56
• 可旋转键数：
  42
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,4R,5R,6S)-2-(phenoxymethyl)-3,6-bis(phenylmethoxy)-4,5-bis[(E)-prop-1-enoxy]cyclohexan-1-ol 、 1,2-di-O-hexadacanoyl-sn-glycerobenzyl (N,N-diisopropylamino)phopshoramidite 生成 [(2S)-2-hexadecanoyloxy-3-[[(1R,2R,3S,4R,5R,6R)-2-(phenoxymethyl)-3,6-bis(phenylmethoxy)-4,5-bis[(E)-prop-1-enoxy]cyclohexyl]oxy-phenylmethoxyphosphanyl]oxypropyl] hexadecanoate
  参考文献：
  名称：

  DREEF, C. E.;ELIE, C. J. J.;HOOGERHOUT, P.;MAREL, G. A. VAN DER;BOOM, J. +, TETRAHEDRON LETT., 29,(1988) N 49, C. 6513-6516

  摘要：

  DOI：
• 作为产物：
  描述：

  双二异丙基氨基氯化磷 在 四氮唑 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 30.5h， 生成 1,2-di-O-hexadacanoyl-sn-glycerobenzyl (N,N-diisopropylamino)phopshoramidite
  参考文献：
  名称：

  Synthesis of 1-O-(1,2-di-O-palmitoyl-sn-glycero-3-phospho)-d-myo-inositol 4,5-bisphosphate: an analogue of naturally occurring (ptd)Ins(4,5)P2

  摘要：

  DOI：

  10.1016/s0040-4039(00)82387-4

文献信息

• Synthesis of dipalmitoyl phosphatidylinositol 3,4-bis(phosphate) and 3,4,5-tris(phosphate) and their enantiomers
  作者：Simon J. A. Grove、Andrew B. Holmes、Gavin F. Painter、Phillip T. Hawkins、Leonard R. Stephens

  DOI：10.1039/a703045b

  日期：——

  The dipalmitoyl derivatives 4 and 5 of 3-phosphorylated myo-inositol phospholipids 2 and 3 and their enantiomers are synthesised from homochiral myo-inositol precursors 6 and 11; they serve as biological probes for cell signal transduction.

  3-磷酸肌醇磷脂2和3的双棕榈酰衍生物4和5及其对应物由同手性肌醇前体6和11合成，它们是细胞信号转导的生物探针。
• Painter, Gavin F.; Grove, Simon J. A.; Gilbert, Lan H., Journal of the Chemical Society. Perkin transactions I, 1999, # 8, p. 923 - 935
  作者：Painter, Gavin F.、Grove, Simon J. A.、Gilbert, Lan H.、Holmes, Andrew B.、Raithby, Paul R.、Hill, Malcolm L.、Hawking, Phillip T.、Stephens, Leonard R.

  DOI：——

  日期：——
• 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.
• Preparation of l-α-phosphatidyl-d-myo-inositol 3-phosphate (3-PIP) and 3,5-bisphosphate (3,5-PIP2)
  作者：J.R. Falck、U.Murali Krishna、Jorge H. Capdevila

  DOI：10.1016/s0960-894x(00)00315-2

  日期：2000.8

  Practical, asymmetric total syntheses of the title phospholipids from a readily available myo-inositol derivative as well as short chain and cross-linkable aminoether analogues are described. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of the D-3 Series of Phosphatidylinositol Phosphates
  作者：Da-Sheng Wang、Ching-Shih Chen

  DOI：10.1021/jo960602u

  日期：1996.1.1

  The 3-mono-, 3,4-bis-, and 3,4,5-trisphosphates of L-alpha-phosphatidyl-D-myo-inositol have been synthesized in their optically active forms from the two enantiomers of 1,2:5,6-di-O-cyclohexylidenemyo-inositol. These chiral precursors were prepared by a facile biocatalytic resolution, in which the 8-butyryl ester of the racemic compound was subjected to enantioselective hydrolysis by porcine pancreatic lipase in a biphasic system. The overall yield from individual chiral precursors ranged from 32% for the 3,4,5-trisphosphate to 39% for the monophosphate.