Diisopropyl-phosphoramidous acid benzyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester | 214068-63-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Diisopropyl-phosphoramidous acid benzyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
• 英文别名: N-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy-phenylmethoxyphosphanyl]-N-propan-2-ylpropan-2-amine
• CAS: 214068-63-0
• 化学式: C₁₉H₃₂NO₄P
• 分子量: 369.441
• InChiKey: ABMIPRUNIQULSC-CPFIQGLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Diisopropyl-phosphoramidous acid benzyl 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 6.0h， 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：

  双二异丙基氨基氯化磷 在 terazole 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 Diisopropyl-phosphoramidous acid benzyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
  参考文献：
  名称：

  通过肌肌醇原苯甲酸酯快速有效地合成磷脂酰肌醇3,4,5-三磷酸

  摘要：

  有效的路线两个磷脂酰肌醇-3,4,5-三磷酸[磷脂酰肌醇（3,4,5）P3 3 ]具有不同酰基链的类似物已经被开发使用廉价地提供肌醇肌醇作为原料。原苯甲酸酯衍生物的高收率，在其脱对称化中优先形成所需的受保护的肌醇非对映异构体和易于分离，使得合成方便，经济且高收率。由于二酰基甘油（DAG）外消旋化的固有问题，具有明确立体化学纯度的磷脂酰肌醇磷酸酯[PIPns]的合成一直很困难。我们的方法排除了DAG单元中发生消旋作用的可能性，因此可以访问PtdIns（3,4,5）P 3光学纯度高。由于最后介绍了酰基官能团，因此所报道的方法适用于具有任何酰基链的PtdIns（3,4,5）P 3的合成（甚至是类似物的文库）。

  DOI：

  10.1016/j.tetlet.2007.01.095

文献信息

• Analogs of Alpha Galactosyceramide and Uses thereof
  申请人：Cerundolo Vincenzo

  公开号：US20090239813A1

  公开（公告）日：2009-09-24

  There are disclosed compound of formula I, in which R 1 represents a hydrophobic moiety adapted to occupy the C′ channel of human CDId, R 2 represents a hydrophobic moiety adapted to occupy the A′ channel of human CDId, such that R 1 fills at least at least 30% of the occupied volume of the C′ channel compared to the volume occupied by the terminal nC 14 H 29 of the sphingosine chain of α-galactosylceramide when bound to human CDId and R 2 fills at least 30% of the occupied volume of the A′ channel compared to the volume occupied by the terminal nC 25 H 51 of the acyl chain of α-galactosylceramide when bound to human CDId R 3 represents hydrogen or OH, R a and R b each represent hydrogen and in addition, when R 3 represents hydrogen, R a and R b together may form a single bond, X represents or —CHA(CHOH) n Y or —P(═0)(0 − )0CH 2 (CH0H) m Y, in which Y represents CHB 1 B 2 , n represents an integer from 1 to 4, m represents 0 or 1, A årepresents hydrogen, one of B 1 and B 2 represents H, OH or phenyl, and the other represents hydrogen or one of B 1 and B 2 represents hydroxyl and the other represents phenyl, in addition, when n represents 4, then A together with one of B 1 and B 2 together forms a single bond and the other of B 1 and B 2 represents H, OH or OSO 3 H and pharmaceutically acceptable salts thereof; the compounds of formula I are indicted for use in the treatment of a virus, microbial infection, parasite, an autoimmune disease, cancer, allergy or asthma
• ANALOGS OF ALPHA GALACTOSYLCERAMIDE AND USES THEREOF
  申请人：Cerundolo Vincenzo

  公开号：US20120034269A1

  公开（公告）日：2012-02-09

  Compounds of formula wherein the variable are defined in the specification, are used in compositions which stimulate T cell responses.
• US8039670B2
  申请人：——

  公开号：US8039670B2

  公开（公告）日：2011-10-18
• US8188313B2
  申请人：——

  公开号：US8188313B2

  公开（公告）日：2012-05-29
• US8334408B2
  申请人：——

  公开号：US8334408B2

  公开（公告）日：2012-12-18