71454-45-0Relevant academic research and scientific papers
Synthesis and schematic mechanism of 3-phenylamino-4-phenyl-5-tetra-O-acetyl-β-D-glucopyranosylimino-1,2,4-dithiazolidines and Its De-acetylated Nucleoside
Hardas, Aruna,Tayade, Priti
, p. 2310 - 2316 (2018)
A systematic synthesis of 3-phenylimino-4-phenyl-5-tetra-O-acetyl-β-D-glucopyranosylimino-1,2,4-dithiazolidine (acetylated glucopyranosylimino nucleoside) from glucose as starting material. The steps included acetylating glucose to glucose penta-acetate (II). Step 2 involves the bromination of glucose penta-acetate (II) to 2,3,4,6 tetra-O-acetyl-α-D-glucopyranosyl bromide (III). In step 3 compound (III) reacted with lead thiocyanate to give 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (IV). In the step 4 N-phenyl-3-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (V) was prepared. In the last step on refluxing compound (V) with N-phenyl S-chloro isothiocarbamoyl chloride to yield acetylated glucopyranosyl nucleoside. Furthermore de-acetylating of acetylated glucopyranosyl nucleoside was carried out to obtain 3-phenylimino-4-phenyl-5-β-D-gluopyranosyl imino 1,2,4-dithiazolidine (de-acetylated glucopyranosylimino nucleoside). The synthesized acetylated glucopyranosylimino nucleoside and deacetylated glucopyranosylimono nucleoside were structurally confirmed by elemental analysis, ultraviolet spectral analysis, infrared spectroscopy, nuclear magnetic resonance spectroscopy and mass spectroscopy.
Thiourea linked peracetylated glucopyranosyl-anthraquinone conjugate as reversible ON-OFF receptor for fluoride in acetonitrile
Areti, Sivaiah,Khedkar, Jayshree K.,Chilukula, Ramakrishna,Rao, Chebrolu P.
, p. 5629 - 5634 (2013/09/23)
A new thiourea linked peracetylated glucopyranosyl-anthraquinone conjugate (L) has been synthesized and characterized. The binding properties of L have been studied with nineteen different anions. The L exhibited selective chromogenic as well as fluorescent chemosensor property toward F- by a ～13-fold increase in the emission intensity upon binding with F -. The minimal detection limit for F- is 185 ± 5 ppb in acetonitrile. Interaction of F- led to a bathochromic shift of 80 nm in the absorption band. An INHIBIT logic gate has been proposed using the output obtained from the fluorescence studies. The structure of the species formed upon the interaction of F- with L has been established by DFT computations.
Comparative study of microwave induced and conventional synthesis of acetylated sugar isothiocyanates and related thiocarbamides
Yadgire, Atul V.,Korpe, Gajanan V.,Deshmukh, Shirish P.
experimental part, p. 1614 - 1619 (2012/05/05)
The synthesis of several acetylated sugar isothiocyanates have been carried out under microwave irradiation in excellent yields of products by using related bromides and lead thiocyanate in sodium dried xylene. Several acetylated sugar thiocarbamides have been synthesized by the interaction of respective acetylated sugar isothiocyanates with appropriate aryl amines under microwave irradiation. Copyright E-Journal of Chemistry 2004-2011.
Assessment of synthetic methods for the preparation of N-β-d-glucopyranosyl-N′-substituted ureas, -thioureas and related compounds
Somsak, Laszlo,Felfoeldi, Nora,Konya, Balint,Huese, Csaba,Telepo, Katalin,Bokor, Eva,Czifrak, Katalin
, p. 2083 - 2093 (2008/12/21)
Preparation of O-peracetylated N-β-d-glucopyranosyl-N′-acyl urea derivatives resulted in the formation of anomeric mixtures under the following conditions: acylation of O-peracetylated β-d-glucopyranosyl urea by acyl chlorides in the presence of ZnCl2 in refluxing CHCl3; addition of O-peracetylated β-d-glucopyranosylamine to acyl isocyanates in acetonitrile at rt; addition of carboxamides to in situ prepared O-peracetylated β-d-glucopyranosyl isocyanate in refluxing toluene. Deprotection of O-peracetylated N-β-d-glucopyranosyl-N′-acyl ureas either under base (NaOMe in MeOH at or below rt) or under acid (KHSO4 or AcCl in MeOH at rt) catalyzed transesterification conditions resulted in unavoidable partial cleavage of the N′-acyl moieties. Reaction of β-d-glucopyranosylammonium carbamate with an isocyanate, isothiocyanate or isoselenocyanate in dry pyridine at rt appears as a general method for the preparation of the corresponding β-d-glucopyranosyl ureas, -thio- and -selenoureas, respectively, inclusive N′-acyl derivatives.
Raney Nickel Desulphuration of 1-Substituted- and 1,3-Disubstituted-thioureas
Ali, M. Umar,Meshram, H. M.,Paranjpe, M. G.
, p. 666 - 669 (2007/10/02)
Certain 1-aryl-1,3-diaryl- and 1-aryl-3-tetra-O-acetyl-β-D-glucopyranosyl thioureas have been successfully desulphurated into the related mono- and 1,3-di-substituted formamidines with the help of Raney nickel catalyst.A few of them have been converted into the corresponding formamides also.Structure of the products have been established through usual chemical transformations, ir, nmr and mass spectral analysis.
