1,3,4,6-Tetra-O-acetyl-a-D-glucopyranose - CAS 4292-12-0
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CAS 4292-12-0 1,3,4,6-Tetra-O-acetyl-a-D-glucopyranose

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Reference Reading

1.Hydrolysis of the GlcNAc oxazoline: deamidation and acyl rearrangement.
Jha R1, Davis JT. Carbohydr Res. 1995 Nov 7;277(1):125-34.
The specific deamidation of 2-acetamido-1,3,4,6-tetra-O-acetyl-alpha-D-glucopyranose is achieved by p-toluenesulfonic acid-promoted hydrolysis of 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucopyrano)-[2,1 -d]-2- oxazoline 2 to give quantitative formation of the 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-alpha-D-glucopyranose p-toluenesulfonate (5d). This two-step procedure provides an amino sugar which may be readily acylated to give novel glycoconjugates. Alternatively, base-catalyzed O-1-->N-2 acyl rearrangement of the amino tosylate 5d gives the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranose 4 as a 9:1 mixture of alpha and beta anomers. Thus, hydrolysis of GlcNAc oxazoline 2 gives the amino-ester 5 as the kinetic product and the amido-alcohol 4 as the thermodynamic product.
2.A concise synthesis of 4-nitrophenyl 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-mannopyranosides.
Popelová A1, Kefurt K, Hlavácková M, Moravcová J. Carbohydr Res. 2005 Jan 17;340(1):161-6.
4-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha- and beta-D-mannopyranosides were prepared from methyl 4,6-O-benzylidene-alpha-D-glucopyranoside and 1,3,4,6-tetra-O-acetyl-alpha-D-glucopyranose, respectively. Chemoselective reduction of both azides with hydrogen sulfide readily afforded 4-nitrophenyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-alpha-D- and -beta-D-mannopyranosides in higher yields than reduction with triphenylphosphine or a polymer-supported triarylphosphine. Subsequent de-O-acetylation yielded 4-nitrophenyl 2-acetamido-2-deoxy-alpha-D-mannopyranoside and 4-nitrophenyl 2-acetamido-2-deoxy-beta-D-mannopyranoside in 20% and 44% overall yields, respectively.
3.Synthesis of a thio analogue of n-propyl kojibioside, a potential glucosidase inhibitor.
Andrews JS1, Pinto BM. Carbohydr Res. 1995 Apr 18;270(1):51-62.
The disaccharide alpha-D-Glc p-(1-S-2)-beta-D-Glc p-(1-OPr) 1, a thio analogue of alpha-D-Glc p-(1 --> 2)-alpha-D-Glc p-(1-OPr)(n-propyl kojibioside) in which the inter-glycosidic oxygen atom is replaced by sulfur, has been synthesized for evaluation as a potential glucosidase inhibitor. Glycosylation of the 2-thiol glucopyranosyl acceptor 4 with the trichloroacetimidate of 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranose 5 gave the alpha-linked disaccharide 6 stereoselectively. Deprotection was performed by hydrogenolysis in the presence of Pd/C to give 1 as the beta-n-propyl glycoside. Glycosylation of the thiol 4 with the trichloroacetimidate of 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranose 8 gave a 1:2.3 mixture if the alpha and beta disaccharides (9 and 10); evidence is presented for the occurrence of the orthoester 11, as an intermediate in the formation of the beta-disaccharide.