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H. Arita, N. Ueda, Y. Matsushima (1972)
The Reduction of Chlorodeoxy Sugars by Tributyltin HydrideBulletin of the Chemical Society of Japan, 45
M. Teichmann, G. Descotes, D. Lafont (1993)
Bromination of 1,5-Anhydrohex-1-enitols (Glycals) Using Quaternary Ammonium Tribromides as Bromine Donors: Synthesis of α-1,2-trans-2-Bromo-2-deoxyglycopyranosyl Bromides and FluoridesSynthesis, 1993
T. Haradahira, M. Maeda, H. Omae, Y. Yano, M. Kojima (1984)
Synthesis of 2-deoxy-2-fluoro-D-mannose using fluoride ion.Chemical & pharmaceutical bulletin, 32 12
M. Michalska, J. Borowiecka, P. Lipka, T. Rokita-Trygubowicz (1989)
Stereoselective synthesis of 5,5-dimethyl-2-oxo-2-(3,4,6-tri-O-acetyl-2-deoxy-α-D-hexopyranosylseleno)-1,3,2-dioxaphosphorinane: novel observations on the selenono–selenolo isomerization of phosphoroselenoatesJournal of The Chemical Society-perkin Transactions 1
Y. Nishikawa, K. Yoshimoto, K. Ashizawa, T. Ikekawa (1981)
Chemical and biochemical studies on carbohydrate esters. XI. Antitumor effects of fatty acid monoesters of D-glucose.Chemical & pharmaceutical bulletin, 29 3
P. Boullanger, G. Descotes (1976)
Additions comparées des halogenès sur le 3,4,6-tri-O-acétyl-1,5-anhydro-1,5-didésoxy-, d-arabino-hex-1-énitol et l'analogue 3,4,6-tri-O-benzylé; effets de solvant sur la formation spécifique des dérivés 1,2-didésoxy-1,2-dihalogéno-α-d-glucopyranosesCarbohydrate Research, 51
G. Sharma, K. Krishnudu (1995)
Radical reactions on carbohydrate acetals: use of a furanoid glycal for the synthesis of cis-fused bicyclic acetalsCarbohydrate Research, 268
J. Borowiecka, M. Michalska (1994)
Efficient Synthesis of 2-Deoxyglycosyl-1-O-Acyl Esters via 2-Deoxyglycosyl Phosphorodithioates as Glycosyl DonorsSynthesis, 1994
C. Glidewell, Elaine Leslie (1977)
Ambidentate nucleophiles. Part 3. Reactions of phosphoroselenoates with molecular halides: the use of 1J(PSe) as a structural diagnosticJournal of The Chemical Society-dalton Transactions
A. Fogh, I. Lundt*, C. Pedersen, P. Rasmussen, L. Nørskov, G. Schroll (1977)
Preparation of Some 2-Bromo-2-deoxy-D-hexopyranoses.Acta Chemica Scandinavica
J. Borowiecka (1999)
NEW DERIVATIVES OF ALPHA - AND BETA -DITHIOPHOSPHATES OF 2-BROMO-2-DEOXY SUGARSPolish Journal of Chemistry, 73
Nobuko Kakiuchi, Masao Hattori, Makoto Nishizawa, Takashi Yamagushi, Takuo Okuda, T. Namba (1986)
Studies on dental caries prevention by traditional medicines. VIII. Inhibitory effect of various tannins on glucan synthesis by glucosyltransferase from Streptococcus mutans.Chemical & pharmaceutical bulletin, 34 2
A. Hussain, J. Truelove, H. Kostenbauder (1979)
Kinetics and mechanism of hydrolysis of 1-(2'-acetoxybenzoyl)-2-deoxy-alpha-D-glucopyranose, a novel aspirin prodrug.Journal of pharmaceutical sciences, 68 3
J. Borowiecka (1999)
Derivatives of?- and?-S-thiophosphates of 2-bromo-2-deoxy-D-hexopyranoseHeteroatom Chemistry, 10
J. Borowiecka, M. Michalska (1996)
Novel Stereoselective Synthesis of Glycosyl-O-Acyl Esters via Peracetylglycosyl Phosphorothioates, -selenoates and -dithioates as Glycosyl DonorsSynthesis, 1996
R. Binkley, D. Bankaitis (1983)
Photochemically Based Synthesis of Deoxy Sugars. Synthesis of 2-Deoxy-D-Arabino-Hexopyranose (2-Deoxy-D-Glucose) and Several of Its Derivatives from 3,4,6-Tri-O-Acetyl-D-GlucalJournal of Carbohydrate Chemistry, 1
J. Borowiecka (1997)
Highly Stereoselective Synthesis of the 1-O-Acylglycosyl Ester of Diclofenac via Glycosyl Phosphorothioates, -Selenoates and -Dithioates as Glycosyl DonorsLiebigs Annalen, 1997
Y. Nishikawa, K. Yoshimoto, M. Ohkawa (1981)
Chemical and Biochemical Studies on Carbohydrate Esters. X. Plant Growth Inhibition by Pure Anomers of Synthetic 1-O-Lauroyl-D-glucopyranoseChemical & Pharmaceutical Bulletin, 29
C. Monneret, P. Choay (1981)
A convenient synthesis of 2-deoxy-d-arabino-hexose and of its methyl and benzyl glycosidesCarbohydrate Research, 96
This work presents the synthesis of glycosyl esters of 2‐bromo‐2‐deoxy‐D‐hexopyranose, having the α‐D‐manno (10a–cα), β‐D‐gluco (11a–dβ) and α‐D‐gluco (11a,bα) configuration, by a stereoselective reaction between phosphoroates 3–8 and carboxylic acids 9a–d. Derivatives of 10a–c and 11a–d are formed in an overall quantitative yield, in an aprotic solvent in the presence of silver salts as a leaving group activator. The phosphoroselenoate of 3 was obtained by the condensation reaction of the triethylammonium salt of phosphoroseleno acid 2 with α‐1,2‐D‐manno‐pyranosyl dibromide 1 with high stereoselectivity. The structures of the compounds 3,10a–c and 11a–d were established by 1H and 13C NMR spectra and by elemental analyses. © 2000 John Wiley & Sons, Inc. Heteroatom Chem 11:292–298, 2000
Heteroatom Chemistry – Wiley
Published: Jan 1, 2000
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