243970-88-9Relevant academic research and scientific papers
An efficient one-stage deprotection/reduction of 1,2-O-isopropylidene furanoses to the corresponding tetrahydrofurans
Ewing, Gregory J.,Robins, Morris J.
, p. 635 - 636 (1999)
(Matrix presented) Treatment of 1,2-O-isopropylidenefuranose derivatives with triethylsilane/boron trifluoride etherate results in generation of the corresponding tetrahydrofurans. This one-stage process removes the 1,2-O-isopropylidene group with accompa
Deoxygenation/dimerization of sugar derivatives with BF3· Et2O-Et3SiH: Synthesis of a β-isonucleoside
Mukherjee, Subhrangshu,Roy, Biswajit G.,Das, Soumendra N.,Mandal, Sukhendu B.
, p. 4929 - 4932,4 (2020/07/31)
Lewis acid-Et3SiH induced deoxygenation of anomeric carbon of sugars generates tetrahydrofuran derivatives, accompanied by hitherto unknown dimeric products. If the reagent addition steps are reversed, tetrahydrofuran derivatives are obtained a
C1-symmetric diphosphite ligands derived from carbohydrates: Influence of structural modifications on the rhodium-catalyzed asymmetric hydroformylation of styrene
Gual, Aitor,Godard, Cyril,Claver, Carmen,Castillon, Sergio
experimental part, p. 1191 - 1201 (2009/07/11)
New 3,5-diphosphite-substituted xylofuranoside (1b, 25a,b, and 26a,b) and glucofuranoside (3a, 7a, 8a,b) ligands with C1 symmetry have been prepared and used in the Rh-catalyzed asymmetric hydroformylation of styrene. The main structural features of these ligands are a) the presence of a 6-O-isopropyl group in ligands with a gluco configuration, b) the absence of 1,2-O-isopropylidene, a common group in many ligands with a furanoside skeleton, c) the presence of an alkyl chain bound to the 2-OH, and d) modification of the diol in the phosphite moiety. Modification of the carbohydrate backbone and diphosphite bridge affects the activity and selectivity of the reaction. Catalytic systems with ligands 1b and 8b were not active at 40 °C, although the formation of the expected hydride species [RhH(CO)2(1b)] was demonstrated by NMR spectroscopy. The highest enantioselectivity (83%) was obtained with the catalytic system Rh/8a. The complex [RhH(CO)2(8a)] was characterized by NMR spectroscopy using high-pressure techniques and was shown to exist in solution as two isomers in equilibrium; the two isomers adopt an equatorial-equatorial (eq-eq) configuration. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
Simple entry into isonucleosides: Synthesis of 6-amino-9-[(3S,4S,5R)-4- hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl]purine
Mereyala, Hari Babu,Mamidyala, Sreeman Kumar
, p. 2965 - 2966 (2007/10/03)
A simple and efficient method for the preparation of isonucleoside 7 is described. The preparation of 1,4-anhydroxylitol 4, a key intermediate, is described by intramolecular cyclization of (2S,3R,4R)-3,5-dibenzyloxypentan-1,2, 4-triol 3 using diethyl car
