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The relation between H-bonding in diequatorial trans-1,2 and axial,equatorial cis-1,2-diols and the regioselectivity of glycosidation by the diazirine 1 was examined. H-Bonds were assigned on the basis of FT-IR and 1H-NMR spectra (Fig. 1). Glycosidation by 1 of the gluco-configurated diequatorial trans-2,3-diols 4-7 yielded the mono-glucosylated products 16/17/20/21 (69-89%); 1,2-/1,3-linked products 37-46:63-54), 24/25/28/29 (60-63%; 1,2-/1,3,-linked products 46-51:54-49), 32-35 (69-94%; 1,2-/1,3-linked products 45-52:55-48), and 36/37/40/41 (59-63%; 1,2-/1,3-linked products 52-59:48-41), respectively (Scheme 1, Table 3). The disaccharides derived from 4, 5, and 7 were characterized as their acetates 18/19/22/23, 26/27/30/31, and 38/39/42/43, respectively. Glycosidation of the galacto-configurated diequatorial 2,3-diols 8 and 9 and the manno-configurated diequatorial 3,4-diol 10 by 1 (Scheme 2, Table 3) also proceeded in fair yields to give the disaccharides 44-47 (69-80%; 1,2-/1,3-linked products ca. 1:1), 48-51 (51-61%; 1,2-/1,3-linked products 54-56:56-54), and 56/57/60/61 (71-80%; 1,3-/1,4-linked products 49-54:51-46), respectively. The 1,3-linked disaccharides 56/57 derived from the diol 10 were characterized as the acetates 58/59. The regio- and stereoselectivities of the glycosidation by 1 were much better for the alpha-D-manno-configurated axial,equatorial cis-2,3-diol 11 and the galacto-configurated axial, equatorial cis-3,4-diol 13 (1,2-/1,3-linked disaccharides ca. 3:7 for 11 and 1,3,-/1,4-linked disaccharides ca. 4:1 for 13; Scheme 3, Table 4). The regio- and stereoselectivity for the beta-D-manno-configurated cis-2,3-diol 12 were, however, rather poor (1,2-/1,3-linked products 48:52). The 1,2-linked disaccharides 66/67 derived from 12 were characterized as the acetates 70/71. Koenigs-Knorr-type glycosidation of the cis-diols 11-13 by 2 or 3 proceeded with a similar regio- and a higher stereoselectivity (alpha-D > beta-D with the donor 2 and alpha-D < beta-D with the donor 3) than with 1, with the exception of 12 which did not react with 2. The regioselectivity of the glycosidations by 1 agrees fully with the H-bonding scheme of the diols and with the hypothesis that the intermediate carbene is preferentially protonated by the most weakly H-bonded OH group. The regioselectivity of the glycosidation by 2 and by 3 is determined by a higher reactivity of the equatorial OH groups and by H-bonding. Several H-bonded and equilibrating isomers of a given diol may intervene in the glycosidation by 1, or 2 and 3, resulting in the same regioselectivity. The low nucleophilicity of 12 and the low degree of regioselectivity in its reaction with 3 show that stereoelectronic effects may also profoundly influence the nucleophilicity of OH groups. If you are hungry for even more, make sure to check my other article about 74808-09-6. Reference of 74808-09-6

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The acyl sulfonamide functional group has been found to serve as a catalytic moiety for the glycosylation of several alcohols when glycosyl donors based on trichloroacetimidates are employed.

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Chemistry is a science major with cience and engineering. The main research directions are chemical synthesis, new energy materials, preparation and modification of special coatings, and research on the structure and performance of functional materials74808-09-6, Name is (2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate, molecular formula is C36H36Cl3NO6. In a Article,once mentioned of 74808-09-6, Formula: C36H36Cl3NO6

A systematic low-temperature NMR study of a glycosylation reaction was performed in the presence of different ionic liquids and acidic catalysts. The influence of the triflate anion derived from [emim][OTf] on the stereochemistry of the glycosylation products was evaluated.

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Photoinduced glycosylation of alcohols with alpha-glucosyl trichloroacetimidates, using aryl urea and thioureas as organo photoacids, was examined under long wavelength UV (ultraviolet) irradiation. The results show, for the first time, that such glycosylations proceed effectively to give the corresponding glycosides in high yields. In addition, high beta-stereoselectivity was obtained under high concentration conditions, whereas high alpha-stereoselectivity was realized under low concentration conditions.

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The fusion-isomeric cellobinoimidazole 2, a potential inhibitor of the syn-protonating beta-glycosidase Cel7A, was synthesised by Koenigs-Knorr glycosylation of the alpha-D-arabinopyranoside 32, followed by selective hydrolysis. Glycosylation of 32 with acetobromoglucose 6 proceeded with poor diastereoselectivity, giving the desired 1,3-linked beta-D-disaccharide 35 as minor product, besides the major 1,3-linked alpha-D-disaccharide 36. Hg 2+-Promoted glycosylation of 32 led predominantly to the 1,2-ortho ester 33. Sequential removal of the silyl, acetyl, and allyl groups of 35 led to a 45:55 equilibrium mixture 2 and the manno-configured isomer 39. Similarly, deprotection of 36 gave a mixture of the maltonoimidazole 42 and the manno-configured isomer 43. According to a known protocol, the glycosyl acceptor 32 was synthesised in eleven steps and an overall yield of 8-13% from D-lyxose. The silylated arabinopyranosyl moiety of the alpha-D-glucosides 13-19, 33, 34, and 36 adopts a 4C1 conformation, while the arabinopyranosyl moiety of the beta-D-glucosides 17 and 35 exists as a 1:3 mixture of 4C1 and 1C4 conformers, as a result of the combined preferred axial orientation of bulky vicinal substituents and the anomeric effect. MM3* Modelling evidences a preferred 4C1 conformation of 35 and 36, and stronger steric interactions between the pyranosyl moieties of 35. The equilibrium mixture 2/39 proved a poor inhibitor of Cel7A with an IC50 value of ca. 4 mM.

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O-Glycosyl trichloroacetimidates transfer the glycosyl moiety to phosphate esters and related A=B-C-H systems highly diastereoselectively.A cyclic transition state for this reaction is also supported by conformational studies.Investigations to possibly generated A-B-C-H type intermediates with alcohol acceptors A-H require a catalyst B=C which reversibly binds A-H.Thus, carbonyl compounds were investigated exhibiting excellent results for chloral as catalyst.

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Enzyme inhibitors cause a decrease in the reaction rate of an enzyme-catalyzed reaction by binding to a specific portion of an enzyme. Irreversible inhibitors are therefore the equivalent of poisons in heterogeneous catalysis. 74808-09-6, C36H36Cl3NO6. A document type is Article, introducing its new discovery., Product Details of 74808-09-6

Cyclohexadienone derivatives possessing alpha-D-glucopyranosyl moiety were designed and synthesized using chemical oxidation or electrochemical oxidation with boron-doped diamond electrode in the final stage. In the chiral induction studies, catalytic hydrogenation provided high diastereoselectivity (dr ratio: > 9:1). Conformational analyses of the C-glucoside structures were performed by NOE experiments and force field calculations, and supported the observed regio-selectivity.

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Catalysts allow a reaction to proceed via a pathway that has a lower activation energy than the uncatalyzed reaction. In homogeneous catalysis, catalysts are in the same phase as the reactants.74808-09-6, C36H36Cl3NO6. A document type is Article, introducing its new discovery., category: Tetrahydropyrans

4-O-(alpha-D-Glucopyranosyl)-alphaHMJ (Glcalpha1,4HMJ), 4-O-(alpha-mannopyranosyl)-alphaHMJ (Manalpha1,4alphaHMJ), 4-O-(alpha-glucopyranosyl)-betaHMJ (Glcalpha1,4betaHMJ), and 4-O-(alpha-mannopyranosyl)-betaHMJ (Manalpha1, 4betaHMJ) were synthesized as endomannosidase inhibitors which are potentially useful both for probing the pathways of N-linked glycoprotein processing and for the chemotherapy of some viral diseases.

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(Matrix Presented) The propargyloxycarbonyl (Poc) group can be used for the selective protection of the hydroxyl function in carbohydrates and can be removed under neutral conditions using tetrathiomolybdate MoS42- (1) in CH3CN at room temperature. Under the conditions of deprotection benzylidine acetals, benzyl ethers, acetyl and levulinoyl esters, and allyl and benzyl carbonates are left untouched. It has also been shown that the new protective group (Poc) is compatible with acidic, basic, and also glycosylation conditions.

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The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.74808-09-6, Name is (2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate, molecular formula is C36H36Cl3NO6. In a Article,once mentioned of 74808-09-6, Recommanded Product: (2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate

Protected propargyl C-glycosides have been prepared by activation of the anomeric centres of 2,3,4,6-tetra-O-benzyl- derivatives of d-glucose and d-galactose, followed by treatment with allenyltributylstannane in the presence of Lewis-acid. Activation was by formation of the anomeric acetates, trichloroacetimidates or fluorides; boron trifluoride etherate and trimethylsilyl trifluoromethanesulfonate were particularly effective Lewis-acids. Attempts to perform similar reactions on 1,2,3,4,6-penta-O-acetyl- d-glucose led to participation by the C-2 acetate group and formation of 3,4,6-tri-O-acetyl-1,2-O-[1-(prop-2-ynyl)ethylidene]-alpha-d-glucopyranose.

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Reference:
Tetrahydropyran – Wikipedia,
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