69892-52-0

Upstream product

• 69892-50-8 methyl 3,4-di-O-benzyl-6-O-triphenylmethyl-2-acetamido-2-deoxy-a-D-glucopyranoside 
• 69892-50-8 N-((3R,4R,5S,6R)-4,5-Bis-benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-3-yl)-acetamide 
• 3055-46-7 N-((4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-acetamide 
• 42756-57-0 methyl 2-acetamido-2-deoxy-6-O-trityl-D-glucopyranoside 
• 72-87-7 N-acetyl-D-glucosamine 
• 3055-46-7 methyl N-acetyl-D-glucosamine 
• 50908-05-9 methyl 6-O-triphenylmethyl-2-acetamido-2-deoxy-α-D-glucopyranoside 
• 6082-04-8 methyl 2-acetylamido-2-deoxy-D-glucoside 

Downstream Products

• 69892-54-2 methyl-(2-acetylamino-O³,O⁴-dibenzyl-O⁶-methyl-2-deoxy-β-D-glucopyranoside) 
• 320343-76-8 4,5,7,8-tetra-O-benzyl-3-deoxy-1-(propane-1,3-diyl-dithioacetal)-α-D-manno-octopyranosyl-(2->6)-(methyl 3,4-di-O-benzyl-2-deoxy-2-N-acetamide-α-D-glucopyranoside) 

Relevant academic research and scientific papers

Design and synthesis of N–acetylglucosamine derived 5a-carbasugar analogues as glycosidase inhibitors

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

A versatile carbohydrate based gelator for oil water separation, nanoparticle synthesis and dye removal

A versatile green gelator suitable for multiple applications is reported. Gelation of organic solvents in a significantly low gelation time (5 s) is achieved. The effect of cooling and sonication on gelation time is investigated. Apart from organic solve

DISAL glycosyl donors for efficient glycosylations under acidic conditions: Application to solid-phase oligosaccharide synthesis

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.

A simple method for the removal of 4-methoxybenzyl group

Removal of 4-methoxybenzyl group from a series of compounds having various protecting groups has been achieved by treatment with 80% acetic acid in water at 80°C for 4 hours.

Stereoselective Preparation of Deuterium-Labeled Sugars: (6R)-(6-2H1)-N-Acetylglucosamine Derivatives

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.

Synthesis of Methyl Glycosides of D-Quinovosamine and D-Fucosamine

Methyl glycosides of D-quinovosamine (7) has been synthesized from D-glucosamine hydrochloride in eight steps.Starting from N-acetyl-D-galactosamine, methyl glycoside of D-fucosamine has been synthesized in six steps.LAH reduction of 6-O-tosyl derivative

REDUCTIVE ONE-STEP ELIMINATION OF AN ACETOXYL RESIDUE AT β-POSITION OF A NITRO GROUP: SYNTHESES OF (-)-SHIKIMIC ACID FROM D-MANNOSE AND 2-DEOXYSTREPTAMINE PENTAACETATE FROM N-ACETYL-D-GLUCOSAMINE

By utilizing a reductive one-step elimination reaction of an acetoxyl residue at β-position of the nitro group in cyclitols, a synthesis of the ketocyclitol triacetate (15a), which was already converted to (-)-shikimic acid (16) and (-)-guinic acid (17), from D-mannose (4) and a conversion from N-acetyl-D-glucosamine (18) to 2-deoxystreptamine pentaacetate (22) have been accomplished.