Benzoyl methyl phosphate as an efficient reagent for the selective monobenzoylation of N-Bz-FTY720

Abstract

A novel and efficient method for the selective monobenzoylation of N-Bz-FTY720 with benzoyl methyl phosphate (BMP) promoted by Zn(OAc)2 and Cs2CO3 was developed. Benzoyl methyl phosphate plays an important role as a biomimetic acylating agent for the monobenzoylation of 1,3-diols.

Lead-Catalyzed Aqueous Benzoylation of Carbohydrates with an Acyl Phosphate Ester

“…The chelated acyl phosphate esters become activated toward the hydroxyls only within the chelated assembly (Scheme ). Recent reports of benzoyl methyl phosphate for the synthesis of a larger scope of compounds have further demonstrated its use as a biomimetic acylating reagent for highly functionalized bioactive substrates. , However, a significant limitation has been the competing catalysis by lanthanides that promotes the hydrolysis of acyl phosphates as an aspect of their general activation of phosphate esters.…”

Catalyst Free Selective Monobenzoylation of Diols with Benzoyl Cyanide: A Robust and Regioselective Strategy

“…Though many protocols for selective protection of hydroxyl groups have emerged in literature [1][2] but procedures that display high levels of substrate generality are still limited barring a few metal catalyzed methods [3][4][5][6] (Scheme 1). Over the years, the protection methods that have been developed include the use of catalysts such as organotin, [7][8][9] organoboron, [10][11] organosilicon, [12][13][14] metal salts, [15][16][17][18][19][20] organobases [21][22][23][24] and enzymes. [25][26][27][28] These catalyst driven reactions not only facilitate the protection of a particular hydroxyl group in polyols, but also realize natural product synthesis or therapeutic agent/s synthesis in a minimum number of steps.…”

Synthesis, Characterization and Antimicrobial Properties of Tri-Schiff's Bases Containing Corephosphorothioate Moiety

“…Phosphorus is known to play an important role in biological systems due to its involvement in the number of metabolic reactions, enzymatic processes, photosynthesis and nucleic acid helices and in several biochemical reactions concerned with the transport and storage of energy. [1][2][3][4] Organophosphorus compounds are well known as one of the most important groups of modern pesticides [5][6][7] .These compounds have attracted much attention of the research community as these possess unique potential biological properties such as antifungal, antibacterial, antileukemic, antiparasitic, antiviral, antiinflammatory, antitumoral, antihypertensive and antioxidant. [7][8][9][10][11][12][13][14][15][16] Moreover, in the recent research,some useful organophosphate esters have been reported [17][18][19] acting as a prodrug which inhibits influenza virus replication in human bronchial epithelial cells and influenza virus-induced expression of many inflammatory cytokines in a PPARγ-dependent (peroxisome proliferator-activated receptor gamma) manner 19 .…”