- METHOD OF PRODUCING GALACTOOLIGOSACCHARIDE, AND INTERMEDIATE THEREOF
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PROBLEM TO BE SOLVED: To provide a method of producing a galactooligosaccharide that may cause the onset of allergic reaction, and an intermediate thereof. SOLUTION: A method of producing a galactooligosaccharide represented by the general formula (1) comprises addition of the 1-position of protected galactobiose to the 6-position hydroxy group of protected lactose of formula (5), and subsequent deprotection of a hydroxy group protecting group. SELECTED DRAWING: Figure 5 COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0051-0052
(2018/04/21)
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- Tertiary Amine Promoted Asymmetric Aldol Reaction of Aldehydes
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The direct asymmetric self-aldol reactions of various α-oxyaldehydes catalyzed by tertiary amines have been demonstrated. By using 10 mol-% of quinine catalyst, dimerization products have been prepared in high yields, with good anti-diastereocontrol, and up to 80% ee. The presented enolate-mediated synthesis of protected tetrose sugars has never been accomplished before by chiral tertiary amine organocatalysts.
- Gut, Bartosz,Mlynarski, Jacek
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supporting information
p. 5075 - 5078
(2015/08/18)
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- Regioselective removal of the anomeric O-benzyl from differentially protected carbohydrates
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A mild, regioselective deprotection of the anomeric O-benzyl from multi-functionally protected carbohydrates via catalytic transfer hydrogenation is described. The protocol is tolerant of O-benzyl and O-benzylidene protections at non-anomeric positions, g
- Jalsa, Nigel Kevin
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supporting information; scheme or table
p. 6587 - 6590
(2012/02/03)
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- Involvement of the S-aglycon in the conformational preferences of thioglucosides
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The conformational preferences of two series of alkyl β-d-thioglucopyranosides in solution were investigated by NMR and CD. The rotamer populations of the hydroxymethyl group were found to depend on the structural nature of the S-aglycon. The population of the gt rotamer increased and that of the gg rotamer decreased as the alkyl group attached to the S atom increased in size. These rotamer populations have a linear correlation with the Taft' steric parameters, the nS s(-) σC s(-) O* exo-anomeric interaction may express these rotational preferences. Comparative analysis of the hydroxymethyl populations between alkyl O- and S-glucosides revealed identical or slightly higher gt and smaller gg populations for the latter compounds.
- Sanhueza, Carlos A.,Dorta, Rosa L.,Vazquez, Jesus T.
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p. 258 - 264
(2008/09/19)
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- Inhibitory effects of Ellagi- and gallotannins on rat intestinal α-glucosidase complexes
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The clove ellagitannins and their related polygalloylglucoses inhibited maltase activity of rat intestinal α-glucosidases. The structure-activity relationship study of those galloylglucoses, varying the extent of galloylation on the glucose core, with the
- Toda, Miou,Kawabata, Jun,Kasai, Takanori
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p. 542 - 547
(2007/10/03)
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- The reaction of partially protected aldoses with stabilized arsonium ylides: Synthesis of E acyclic unsaturated derivatives and C-glycosyl derivatives
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The reaction of partially protected aldoses with (carbomethoxymethyl)triphenylarsonium bromide and zinc in toluene gave E α,β-unsaturated acyclic esters. When intramolecular transesterification occurred, bicyclic 1,4-lactone derivatives were formed concurrently. Otherwise, using these non alcaline conditions, olefination did not favour the formation of C-glycosyl derivatives. On the other hand, when the reaction was performed with (carbomethoxymethylene)triphenylarsorane in toluene, followed by the addition of n-butyllithium, bicyclic derivatives were obtained rapidly in good yields. Moreover, when cyanomethyltriphenylarsonium bromide was used in place of (carbomethoxymethyl)triphenylarsonium bromide, the corresponding E aldooctenonitriles were produced in satisfactory yields.
- Lievre, Catherine,Frechou, Catherine,Demailly, Gilles
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- A new approach to some 1,6-dideoxy 1,6-epithio sugars
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The treatment of hexopyranosyl bromides, also activated at C6 (Br, OTs, OMs), with H2S/HCONMe2 under basic conditions gives rise to 1,6-dideoxy 1,6-epithio sugars. One such sugar has been further transformed into the synthetically useful 3,4-anhydro-1,6-dideoxy-1,6-epithio-β-D-galactose. The treatment of this epoxide with sodium azide and with cyclohexylamine is described. An analogous treatment of one doubly activated hexopyranosyl bromide with sodium hydrogen selenide has led to a novel 1,6-dideoxy 1,6-episeleno sugar which displayed interesting n.m.r. spectra. Finally, in an attempt to prepare 1,6-dideoxy 1,6-epidithio sugars, a tetraalkylammonium tetrathiomolybdate reagent was found to be the reagent of choice for converting doubly activated hexopyranosyl bromides into 1,6-dideoxy 1,6-epithio sugars.
- Driguez, Hugues,McAuliffe, Joseph C.,Stick, Robert V.,Tilbrook, Matthew G.,Williams, Spencer J.
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p. 343 - 348
(2007/10/03)
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- CD and 1H NMR Study of the Rotational Population Dependence of the Hydroxymethyl Group in β Glucopyranosides on the Aglycon and Its Absolute Configuration
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The rotamer population around the C5-C6 bond of chiral and nonchiral alkyl β-glucopyranoside derivatives proved to be dependent on the structure of the aglycon; the population of the gg and gt rotamers decreased and increased, respectively, as the pK
- Morales, Ezequiel Q.,Padron, Juan I.,Trujillo, Mar,Vazquez, Jesus T.
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p. 2537 - 2548
(2007/10/02)
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