benzyl methyl N,N-diisopropylphosphoramidite | 173170-93-9

• 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: benzyl methyl N,N-diisopropylphosphoramidite
• 英文别名: (BnO)(OCH3)PN(iPr)2；N-[methoxy(phenylmethoxy)phosphanyl]-N-propan-2-ylpropan-2-amine
• CAS: 173170-93-9
• 化学式: C₁₄H₂₄NO₂P
• 分子量: 269.324
• InChiKey: OXJFVYQHFGQFDO-UHFFFAOYSA-N

物化性质

• 沸点：
  273.0±19.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl methyl N,N-diisopropylphosphoramidite 在 四氮唑 、 次氯酸叔丁酯 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 12.5h， 生成 dibenzyl methyl phosphate
  参考文献：
  名称：

  Reactions of benzyl methyl substituted-benzyl phosphites with <i>tert</i>-butyl hypochlorite: "balanced TS" validating reactivity/selectivity principle

  摘要：

  DOI：

  10.1139/cjc-76-6-836
• 作为产物：
  描述：

  二异丙胺 在 N,N-二异丙基乙胺 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 benzyl methyl N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  Synthesis and Structure of Cellular Mediators: Inositol Polyphosphate Diphosphates

  摘要：

  The first total syntheses of 1-O-[(phosphonooxy)hydroxyphosphinyl]-2,3,4,5,6-pentakis-O-phosphono-D- myo-inositol (10) and its antipode (11) were achieved from enantiopure 2,3:5,6-di-O-cyclohexylidene-D-myo-inositol (6). The critical pyrophosphate function was introduced, in the presence of flanking phosphate triesters, by mild LiCN-mediated cleavage of a mixed phosphate methyl ester, isolation of the resultant lithium salt, and addition to dibenzyl chlorophosphonate. The benzyl esters were removed by catalytic hydrogenolysis over Pd in t-BuOH/H2O in the presence of NaHCO3. Comparisons of synthetic and enzyme-devived pyrophosphates with two phosphatases suggests natural material has the stereochemical configuration in 10.

  DOI：

  10.1021/ja00154a017

文献信息

• Stereoselective synthesis of the head group of archaeal phospholipid PGP-Me to investigate bacteriorhodopsin–lipid interactions
  作者：Jin Cui、Satoshi Kawatake、Yuichi Umegawa、Sébastien Lethu、Masaki Yamagami、Shigeru Matsuoka、Fuminori Sato、Nobuaki Matsumori、Michio Murata

  DOI：10.1039/c5ob01252j

  日期：——

  Phosphatidylglycerophosphate methyl ester (PGP-Me), a major constituent of the archaeal purple membrane, is essential for the proper proton-pump activity of bacteriorhodopsin (bR).

  磷脂甘油磷酸甲酯（PGP-Me）是古菌紫膜的主要成分，对于细菌紫质蛋白（bR）的正确质子泵活性至关重要。
• Development of inositol-based antagonists for the<scp>d</scp>-myo-inositol 1,4,5-trisphosphate receptor
  作者：Neil S. Keddie、Yulin Ye、Tashfeen Aslam、Tomas Luyten、Davide Bello、Clive Garnham、Geert Bultynck、Antony Galione、Stuart J. Conway

  DOI：10.1039/c0cc03003a

  日期：——

  The syntheses of four D-myo-inositol 1,4,5-trisphosphate (InsP3) derivatives, incorporating phosphate bioisosteres at the 5-position, are reported. The methyl phosphate ester and sulfate derivatives retain InsP3receptor (InsP3R) agonist activity; the compounds that possess a methylphosphonate or a carboxymethyl moiety are InsP3R antagonists.

  报告了四种D-肌醇1,4,5-三磷酸（InsP3）衍生物的合成，其中在5位上结合了磷酸生物异构体。甲基磷酸酯和硫酸盐衍生物保留了InsP3受体（InsP3R）激动剂活性；含有甲基磷酸酯或羧甲基部分的化合物是InsP3R拮抗剂。
• Synthesis of 2- and 5-diphospho-myo-inositol pentakisphosphate (2- and 5-PP-InsP5), intracellular mediators
  作者：Komandla Malla Reddy、K.Kishta Reddy、J.R. Falck

  DOI：10.1016/s0040-4039(97)01088-5

  日期：1997.7

  The title pyrophosphates were prepared in good overall yield from a readily available bis-disiloxanylidene derivative of myo-inositol.

  从容易获得的肌醇的双-二硅氧杂亚环衍生物制备高产率的标题焦磷酸盐。
• Photo-Arbuzov rearrangement route to acyclic nucleoside benzylphosphonates
  作者：Khairuzzaman B. Mullah、Wesley G. Bentrude

  DOI：10.1021/jo00026a008

  日期：1991.12

  The recently discovered photo-Arbuzov rearrangement was carried out with a series of tert-butyldimethyl-silyl-protected dimethyl benzyl phosphites, 9, 15, 18, 20, and 22, easily derived from alcohol precursors, to afford the corresponding dimethyl benzylphosphonates in 67-74% isolated yields. One of the phosphonates, 10, was further converted to the primary bromide which underwent reaction with the sodium salts of adenine, cytosine, and 2-amino-6-chloropurine to give the desired N-alkylated acyclic nucleoside dimethyl benzylphosphonates. The 2-amino-6-chloro compound was further elaborated to the guaninyl and 2,6-diamino derivatives. Demethylation afforded the acyclic nucleoside-based benzylphosphonic acids 25, 27, 29, 31, and 32 in good overall yields. These molecules are closely related structurally to the active antiviral 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) and the potent human erythrocyte purine nucleoside phosphorylase (PNP) inhibitors 9-(5-phosphonopentyl)guanine and 9-(5,5-difluoro-5-phosphonopentyl)guanine.
• Reactions of benzyl methyl substituted-benzyl phosphites with &lt;i&gt;tert&lt;/i&gt;-butyl hypochlorite: "balanced TS" validating reactivity/selectivity principle
  作者：Sung Soo Kim、Yu Zhu、In Seok Oh、Chang Gyeong Lim

  DOI：10.1139/cjc-76-6-836

  日期：——