A Simple and Convenient Synthesis of Glycosyl Azides

Ibatullin, Farid M.; Shabalin, Konstantin A.

doi:10.1080/00397910008086908

Cited by 30 publications

(35 citation statements)

References 12 publications

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“…In the first step (i) GlcNAc was converted to intermediate 1 according to Horton [23]. Subsequent conversion of 1 (ii) to 2a was performed according to Ibatullin [24] and (iii) to 2b and c via a Koenigs-Knorr [25][26][27] glycosidation. In a selective deprotection (iv) Zemplén [28] glycosides 3a-d were obtained.…”

Section: Chemical Synthesis Of Functionalizeď -N-acetylglucosaminidesmentioning

confidence: 99%

Chemo-enzymatic synthesis of functionalized oligomers of N-acetyllactosamine glycan derivatives and their immobilization on biomaterial surfaces

Adamiak

Anders

Henze

et al. 2012

Journal of Molecular Catalysis B: Enzymatic

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Section: Chemical Synthesis Of Functionalizeď -N-acetylglucosaminidesmentioning

confidence: 99%

Chemo-enzymatic synthesis of functionalized oligomers of N-acetyllactosamine glycan derivatives and their immobilization on biomaterial surfaces

Adamiak

Anders

Henze

et al. 2012

Journal of Molecular Catalysis B: Enzymatic

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“…In the present work, acetylated glycosyl azides17 were chosen as starting material. The fully acetylated β‐ D ‐glycosyl azides ( 1 – 8 ) were obtained by the displacement of their corresponding α‐chlorides18 with NaN 3 in aqueous acetone at room temperature 19…”

Section: Resultsmentioning

confidence: 99%

Exploring the Effect of Bioisosteric Replacement of Carboxamide by a Sulfonamide Moiety on N‐Glycosidic Torsions and Molecular Assembly: Synthesis and X‐ray Crystallographic Investigation of N‐(β‐D‐Glycosyl)sulfonamides as N‐Glycoprotein Linkage Region Analogues

Srivastava

Varghese

Loganathan

2013

Chemistry A European J

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N-Glycoprotein linkage region constituents, 2-acetamido-2-deoxy-β-D-glucopyranose (GlcNAc) and asparagine (Asn) are conserved among all the eukaryotes. To gain a better understanding for nature's choice of GlcNAcβAsn as linkage region constituents and inter- and intramolecular carbohydrate-protein interactions, a detailed systemic structural study of the linkage region conformation is essential. Earlier crystallographic studies of several N-(β-glycopyranosyl)alkanamides showed that N-glycosidic torsion, φN , is influenced to a larger extent by structural variation in the sugar part than that of the aglycon moiety. To explore the effect of the bioisosteric replacement of a carboxamide group by a sulfonamide moiety on the N-glycosidic torsions as well as on molecular assembly, several glycosyl methanesulfonamides and glycosyl chloromethanesulfonamides were synthesized as analogues of the N-glycoprotein linkage region, and crystal structures of seven of these compounds have been solved. A comparative analysis of this series of crystal structures as well as with those of the corresponding alkanamido derivatives revealed that N-glycosidic torsion, φN, does not alter significantly. Methanesulfonamido and chloromethanesulfonamido derivatives of GlcNAc display a different aglycon conformation compared to other sulfonamido analogues. This may be due to the cumulative effect of the direct hydrogen bonding between N1 and O1' and C-H···O interactions of the aglycon chain, revealing the uniqueness of the GlcNAc as the linkage sugar.

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“…Glycosyl isocyanides 9, [22] 13a, and 13b were prepared according to Scheme 1. Tetraacetyl-β-glucosyl azide 6, [23] was converted into the corresponding formamidic derivative 8 after hydrogenation and an in situ reaction with freshly prepared acetoformic anhydride. [24] The 1 H NMR spectrum shows that 8 was obtained as a pure β anomer but as a mixture of (E) and (Z) diastereoisomers, due to the iminic form of the formamido group.…”

Section: Resultsmentioning

confidence: 99%

“…Flash chromatography was performed on BDH silica gel (40Ϫ63 µm particle size). TLC was performed on Merck silica gel 60 F 254 plates, and visualized by charring either with a mixture of 96% sulfuric acid (50 mL), methanol (450 mL) and H 2 O (450 mL) or with a solution of (NH 4 ) 6 (9): [22] A solution of compound 6 [23] (1.87 g, 5.01 mmol), a catalytic amount of palladium on activated charcoal and TEA (2.1 mL, 15.0 mmol) and a mixture of diethyl ether/hexane (2:1; 100 mL) was stirred under hydrogen for 3 h. The reaction was monitored by TLC (pure EtOAc) and the spot corresponding to the azido compound disappeared. Meanwhile, a solution of acetoformic anhydride was prepared by heating a solution of acetic anhydride (10 mL, 100 mmol) and formic acid (6 mL, 150 mmol) at 60°C for 3 h. The resulting solution was cooled to room temperature, then added to the amine solution and left under vigorous stirring overnight.…”

Section: Methodsmentioning

confidence: 99%