79386-43-9Relevant academic research and scientific papers
Synthesis and Transformation of Sugar Phosphates
Bogusiak, J.,Szeja, W.
, p. 2181 - 2186 (2007/10/02)
Sugar diphenyl phosphates can be conveniently prepared by the treatment of monosaccharides with diphenylphosphorochloridate under phase-transfer conditions. Key words: synthesis, phosphorylation, sugar phosphates, catalytic two-phase system, thiosugars
Synthesis of glycosyl phosphates and azides
Sabesan,Neira
, p. 169 - 185 (2007/10/02)
Anomerically enriched diphenyl hexopyranosyl phosphate triesters have been prepared from O-alkyl and -acylated hexopyranoses, using diphenyl chlorophosphate and 4-N,N-dimethylaminopyridine. Glycosyl phosphate triesters of D-gluco-, D-galacto-, D-manno, 2-acetamido-2-deoxy-D-gluco-, L-fuco-, and L-rhamno-pyranosyl derivatives have been obtained by this procedure. At temperatures 0° and above, and under thermodynamic control, diphenyl glycosyl phosphates cis to the pyranosyl C-2 substituent are formed predominantly, whereas at low temperatures and under kinetic control, glycosyl phosphate triesters having 2-trans stereochemistry are obtained. The β-glycosyl phosphate triesters of D-glucose and D-galactose derivatives are unstable and undergo anomerization to the α-glycosyl phosphate triesters, in contrast to the stable β-phosphate derivatives of L-rhamnose and D-mannose. These phosphate triesters have been deprotected to glycosyl phosphate triethylammonium salts, suitable for the preparation of other key biological derivatives, such as nucleotide sugars. In addition, the diphenyl phosphate groups at the anomeric center have been displaced by azide togive the glycosyl azides, key intermediates in the synthesis of glycosyl amino acids. Anomerically enriched diphenyl hexopyranosyl phosphate triesters have been prepared from O-alkyl and -acrylated hexopyranoses, using diphenyl chlorophosphate and 4-N,N-dimethylaminopyridine. Glycosyl phosphate triesters of D-gluco-, D-galacto-, D-manno, 2-acetamido-2-deoxy-D-gluco-, L-fuco-, and L-rhamno-pyranosyl derivatives have been obtained by this procedure. At temperatures 0° and above, and under thermodynamic control, diphenyl glycosyl phosphates cis to the pyranosyl C-2 substituent are formed predominantly, whereas at low temperatures and under kinetic control, glycosyl phosphate triesters having 1,2-trans stereochemistry are obtained. The β-glycosyl phosphate triesters of D-glucose and D-galactose derivatives are unstable and undergo anomerization to the α-glycosyl phosphate triesters, in contrast to the stable β-phosphate derivatives of L-rhamnose and D-mannose. These phosphate triesters have been deprotected to glycosyl phosphate triethylammonium salts, suitable for the preparation of other key biological derivatives, such as nucleotide sugars. In addition, the diphenyl phosphate groups at the anomeric center have been displaced by azide to give the glycosyl azides, key intermediates in the synthesis of glycosyl amino acids.
Glycosyl Imidates, 10. - Glycosyl Phosphates from Glycosyl Trichloroacetimidates
Schmidt, Richard R.,Stumpp, Michael
, p. 680 - 691 (2007/10/02)
The glycosyl trichloroacetimidates 1-α,β, 8-α, 11-α, 13-α, 15-α, and 17-α directly transfer the glycosyl moiety to phosphoric acid mono- and diesters.The acidity of the phosphoric acid derivatives used was sufficient for the activation of the trichloroacetimidates, therefore an additional acidic catalyst was not required.From the β-imidate 1-β α-glycosyl phosphate and from the α-imidates preferentially β-glycosyl phosphates were obtained.Reaction of dibenzyl phosphate (2a) and cetyl phosphate (2c) with 1-α demonstrated that β/α-anomerization iscatalyzed by traces of acid.The glycosyl phosphates 3a-α, 3a-β - 3c-β, 3f-α, 9a-β, and 9c-β were partly or totally deprotected.The structures of the synthezised compounds were assigned by 1H NMR spectroscopy and by comparison with literature data.
USE OF O-THALLIUM(I) SALTS IN THE SYNTHESIS OF PHOSPHATE, SULFITE, AND RELATED ESTER DERIVATIVES OF CARBOHYDRATES
Granata, Alessandro,Perlin, Arthur S.
, p. 165 - 172 (2007/10/02)
O-Thallium(I) salts are shown to promote a variety of rapid, high-yield, substitution reactions at an anomeric, a primary, or a secondary position of carbohydrate derivatives.Synthesis are described of phosphates, phosphites, sulfites, and xanthic ester d
