104022-77-7Relevant academic research and scientific papers
Regioselective Monoesterification Study of the Diol in 1-C-(4,6-O-Benzylidene-β-D-glucopyranosyl) Acetone
Zhang, Tao,Wang, Tianyi,Fang, Zhijie
, p. 2567 - 2575 (2015)
1-C-(4,6-O-Benzylidene-β-D-glucopyranosyl) acetone has been studied in a catalytic system consisting of triethylamine-p-dimethylaminopyridine (TEA-DMAP) in the presence of a number of esterification reagents in dichloromethane. It was found that all-protected and monoprotected products form simultaneously. However, the regioselectivity tends to favor the 3-substituted derivative. Structural parameters have been determined by 1H NMR, 13C NMR, 1H-1H correlation spectroscopy, and elemental analysis. Furthermore, a possible mechanism for the formation of intramolecular hydrogen-bond networks between the carbonyl group and 2-OH was described. The energy changes of the transition state in this reaction, as determined by a molecular modelling study, provided further evidence to assign the relative reactivities of each individual hydroxyl group.
Synthesis of an allergy inducing tetrasaccharide “4P-X”
Moriya, Takashi,Nagahata, Naoki,Odaka, Rei,Nakamura, Hirohide,Yoshikawa, Jun,Kurashima, Katsumi,Saito, Tadao
, p. 44 - 49 (2017)
4P-X (β-D-galactopyranosyl-(1?→?4)-β-D-galactopyranosyl-(1?→?6)-[β-D-galactopyranosyl-(1?→?4)]-β-D-glucopyranose) is included in galacto-oligosaccharides (GOSs) produced by β-galactosidase derived from Bacillus circulans. 4P-X has been known to induce particularly strong allergies. High purity 4P-X is essential for use as a standard to quantify the amount of 4P-X in GOSs; however, the isolation of high purity 4P-X has never been reported. In this study, we achieved the synthesis of 4P-X by a combination of organic and enzymatic chemical syntheses in a short time. This is the first report of isolated, high purity 4P-X.
Inhibitory effects of Ellagi- and gallotannins on rat intestinal α-glucosidase complexes
Toda, Miou,Kawabata, Jun,Kasai, Takanori
, p. 542 - 547 (2001)
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
Synthesis of a nitrogen analogue of salacinol and its α-glucosidase inhibitory activity
Muraoka,Ying,Yoshikai,Matsuura,Yamada,Minematsu,Tanabe,Matsuda,Yoshikawa
, p. 1503 - 1505 (2001)
A nitrogen analogue 4 of the naturally occurring sulfoniumion salacinol (1), a potent α-glucosidase inhibitor isolated from the Ayruvedic medicine Salacia reticulata, was synthesized and its inhibitory activity against α-glucosidase tested. Substitution o
A new approach to some 1,6-dideoxy 1,6-epithio sugars
Driguez, Hugues,McAuliffe, Joseph C.,Stick, Robert V.,Tilbrook, Matthew G.,Williams, Spencer J.
, p. 343 - 348 (1996)
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.
Synthesis of photolabile group protected anomeric acetals and its application in carbohydrate synthesis with the assistance of continuous flow photo-reactor
Tiwari, Varsha,Badavath, Vishnu Nayak,Singh, Adesh Kumar,Kandasamy, Jeyakumar
, p. 227 - 236 (2020/03/18)
Selective deprotection of photolabile anomeric 2-nitrobenzyl acetals was achieved using continuous flow photo-reactor (UV radiation at 355 nm) in methanol-water. Various protecting groups such as acetyl, benzyl, benzoyl, benzylidine, TBS, etc. were found to be highly stable during the photolysis.
An Improved, Versatile, and Easily Scalable Synthesis of Sphingomyelins: Application to Stable Isotope Labeling
Blankenstein, J?rg,Le Strat, Franck,Pérard, Serge,Philippe, Nicolas,Roy, Sébastien
supporting information, p. 2106 - 2110 (2020/08/17)
With a view to make conveniently labeled mass spectrometry standards available, a set of deuterated sphingomyelins were prepared by a new expedient, flexible, robust, scalable, and high-yielding synthetic scheme starting from 2-azido-3- O -benzoylsphingos
NATURAL AND SYNTHETIC DITERPENE GLYCOSIDES, COMPOSITIONS AND METHODS
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Page/Page column 99; 128, (2019/08/12)
Novel diterpene glycosides isolated from Stevia extract as well as diterpene glycosides that are synthetically prepared are provided herein. Compositions and consumables comprising the novel diterpene glycosides are also provided herein. Methods of enhancing the sweetness and/or flavor of consumables using the novel diterpene glycosides, methods of preparing compositions and consumables comprising the novel diterpene glycosides, methods of purifying the novel diterpene glycosides and methods of synthesizing the diterpene glycosides are also provided.
METHOD OF PRODUCING GALACTOOLIGOSACCHARIDE, AND INTERMEDIATE THEREOF
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Paragraph 0051-0052, (2018/04/21)
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
Oligosaccharide compound and its manufacture and its intermediate
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Paragraph 0237; 0238; 0239, (2018/04/14)
The purpose of the present invention is to provide an oligosaccharide with high versatility that can produce a protected sulfate oligosaccharide that can become a manufacturing intermediate of polysulfated hyaluronic acid, and to provide a manufacturing method therefor and an intermediate thereof. Position 2 amino groups in glucosamine, galactosamine, and the like can react with saccharide receptors having an electron attracting group such as glucuronic acid and protected sulfate groups, by using a saccharide donor protected by a specific protective group.
