128984-82-7

Upstream product

• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 100-46-9 benzylamine 
• 225923-18-2 N-Benzyl-2,3,4,6-tetra-O-benzyl-D-xylo-hex-5-ulosonamide 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 

Downstream Products

• 1414930-64-5 (2R,3S,4R,5R)-N-benzyl-2,3,4,6-tetrabenzyloxy-5-triethylsiloxyhexanamide 
• 1414930-68-9 C₅₂H₆₅NO₈Si 
• 1414930-59-8 (2R,3S,4R,5R)-N-{(S)-1-allyloxycarbonyl-2-phenylethyl}-2,3,4,6-tetrabenzyloxy-5-{(S)-2-tertbutoxycarbonamidopropionyloxy}hexanamide 
• 1414930-72-5 (2R,3S,4R,5R)-N-{(S)-1-ethoxycarbonyl-2-phenylethyl}-2,3,4,6-tetrabenzyloxy-5-triethylsiloxyhexanamide 
• 13096-63-4 2,3,4,6-Tetra-O-benzyl-N,N-dimethyl-D-gluconamid 
• 225923-18-2 N-Benzyl-2,3,4,6-tetra-O-benzyl-D-xylo-hex-5-ulosonamide 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 

Relevant academic research and scientific papers

Synthesis of glycosylamines and glyconamides using molecular iodine

We describe herein the synthesis of glyconamides and glycosylamines usingmolecular iodine on benzylated carbohydrates. During the improvement and the optimization of the direct oxidative amidation reaction,we also discovered the possibility to form glycosylamines with excellent yields and short reaction times in comparison with the previously reported procedures. Advantages of these methods are the operational simplicity, elimination of use of complicated reagents and procedures, and generality of the reactions. Our methodology is an excellent access to precursors of N-alkyliminosugars and imino-C-glycosides.

Synthesis of protected sugar-amino acid hybrid molecules as platform for further derivatization

The sugar-amino acid hybrid molecules with appropriate protecting groups were synthesized from sugar-derived lactones and ester of amino acids in five high yielding steps. The C-5 of the resultant hybrid molecule, upon selective deprotection, can be further derivatized to afford the linear depsipeptide.

Metal-free one-pot oxidative amidation of aldoses with functionalized amines

(Chemical Equation Presented) Metal-free one-pot oxidative amidation of aldoses with functionalized amines using iodine provides a rapid access to functionalized aldonamides. The main advantage of this approach relies on the fact that aldehyde oxidation and C-N bond formation are performed in a single synthetic operation.

Cyclization dichotomy of D-xylo-hex-5-ulosonamides and synthesis of piperidine analogs of aldohexoses and aldohexono-1,5-lactones

The preparation of 2,3,4,6-tetra-O-benzyl-S-D-xylo-hex-5-ulosonamides 3a and 3b and their cyclization to 5-amino-2,3,4,6-tetra-O-benzyl-5-deoxy-D-glucono-1,5-lactam (4) and 5-amino-2,3,4,6-tetra-O-benzyl-S-deoxy-D-talono-1,5-lactam (5) or to 2,3,4,6-tetra