69892-52-0Relevant articles and documents
Design and synthesis of N–acetylglucosamine derived 5a-carbasugar analogues as glycosidase inhibitors
Narayana, Chintam,Kumari, Priti,Ide, Daisuke,Hoshino, Nasako,Kato, Atsushi,Sagar, Ram
, p. 1957 - 1964 (2018/03/21)
An efficient synthesis of new six-membered carbasugars in both L-form and D-form starting from N–acetylglucosamine is described. The key synthetic steps involved regioselective protection and deprotection, Ferrier carbocyclization, Peterson olefination, h
DISAL glycosyl donors for efficient glycosylations under acidic conditions: Application to solid-phase oligosaccharide synthesis
Petersen,Jensen
, p. 2175 - 2182 (2007/10/03)
The use of DISAL (methyl dinitrosalicylate) glycosyl donors in efficient Lewis acid-promoted glycosylations is reported. N-Acetyl-D-glucosamine monosaccharide acceptors are successfully glycosylated at O-6 or O-4 using benzyl- and benzoyl-protected DISAL donors in CH2Cl2 or nitromethane in the presence of LiClO4. The resultant disaccharides are isolated in yields ranging from 35 to 93%. Other Lewis acids such as FeCl3, TMSOTf, or BF3·Et2O also prove efficient for glycosylation of the secondary alcohol cyclohexanol. However, for the synthesis of disaccharides, the mild activation by LiClO4 gives higher yields. This approach is extended to efficient solid-phase glycosylation of a D-glucosamine derivative anchored by the 2-amino group through a Backbone Amide Linker (BAL) to a polystyrene support.
Stereoselective Preparation of Deuterium-Labeled Sugars: (6R)-(6-2H1)-N-Acetylglucosamine Derivatives
Falcone-Hindley, Margaret L.,Davis, Jeffery T.
, p. 5555 - 5561 (2007/10/03)
The preparation of methyl (6R)-(6-2H1)-2-deoxy-2-N-acetamido-α-D-glucose (8α-d) and methyl (6R)-(6-2H1)-2-deoxy-2-N-acetamido-β-D-glucose (8β-d) is described. The key step in the synthesis was the stereoselective reduction of a C6-aldehydo-GlcNAc derivative with (R)-(+)-Alpine-Borane-d. Reduction of either methyl 6-aldehydo-3,4-di-O-benzyl-α-GlcNAc (6α) or methyl 6-aldehydo-3,4-di-O-benzyl-β-GlcNAc (6β) using (R)-(+)-Alpine-Borane-d in CH2Cl2 was significantly more stereoselective (>15:1 stereoselectivity for both anomers) than was reduction with NaBD4 in MeOH. The absolute stereochemistry at C6 of the deuterated GlcNAc derivatives was determined from 1H NMR analysis of the conformationally locked sugars, methyl (6R)-(6-2H 1)-4,6-O-benzylidene-2-deoxy-2-N-acetamido-α-D-glucose (9α-d) and methyl (6R)-(6-2H 1)-4,6-O-benzylidene-2-deoxy-2-N-acetamido-β-D-glucose (9β-d). Comparison of 3JH5,H6 values and 1H-1H NOEs for the nondeuterated and deuterated benzylidene derivatives showed that reduction with (R)-(+)-Alpine-Borane-d gave the (6R)-(G-2H1) epimer as the major product for both the GlcNAc α and β methyl glycosides. This stereoselective reduction enabled the 1H NMR signals for the prochiral H6 and H6′ protons in a series of GlcNAc derivatives to be assigned.
