106265-18-3

Upstream product

• 4704-15-8 ((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester 
• 100-39-0 benzyl bromide 
• 102997-59-1 2-amino-N-benzyl-N-benzyloxycarbonyl-3,4-di-O-benzyl-2-deoxy-1-O-methyl-α-D-gluco-hex-5-enopyranoside 
• 93000-10-3 benzyl ((2R,4aR,6S,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl hexahydropyrano[3,2-d][1,3]dioxin-7-yl)carbamate 
• 129095-43-8 methyl 4,6-O-benzylidene-3-O-benzyl-2-(N-benzyl-N-benzyloxycarbonyl-amino)-2-deoxy-α-D-glucopyranoside 
• 129117-17-5 methyl 3-O-benzyl-2-(N-benzyl-N-benzyloxycarbonylamino)-2,6-dideoxy-6-iodo-α-D-glucopyranoside 
• 129095-44-9 methyl 3-O-benzyl-2-(N-benzyl-N-benzyloxycarbonylamino)-2-deoxy-α-D-glucopyranoside 

Downstream Products

• 121843-64-9 1D-(1,2,4/3) 3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-methoxymethylene-1,3,4-cyclohexanetriol 
• 106265-20-7 1D-(1,2,4/3)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-methylene-1,3,4-cyclohexanetriol 
• 106265-21-8 1D-(1,2/3)-3-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-C-hydroxy-methyl-cyclohex-4-en-1,3-diol 
• 106295-31-2 1D-(1,2,4,5/3)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-C-hydroxy-methyl-1,3,4-cyclohexanetriol 
• 106265-22-9 (1S,2S,3R,4R,5R)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-C-hydroxymethyl-1,3,4-cyclohexanetriol 
• 246034-43-5 carba-α-D-glucosamine 
• 143465-64-9 (1S,2S,3R,4R,5R)-3,4-di-O-benzyl-2-benzylamino-5-C-hydroxymethyl-1,3,4-cyclohexanetriol 
• 143564-22-1 (1S,2S,3R,4R,5R)-2-amino-5-C-hydroxymethyl-1,3,4-cyclohexanetriol hydrochloride 
• 106265-19-4 (1S,2S,3R,4R)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-methoxymethylene-1,3,4-cyclohexanetriol 
• 143465-47-8 1D-(1,2,4/3,5)-3-O-<(R)-3-hydroxytetradecanoyl>-2-<(R)-3-hydroxytetradecanoylamido>-1-O-phosphono-5-C-hydroxymethyl-1,3,4-cyclohexanetriol 
• 143465-60-5 (R)-3-Benzyloxymethoxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aR)-7-((R)-3-benzyloxymethoxy-tetradecanoylamino)-6-(diphenoxy-phosphoryloxy)-2-phenyl-hexahydro-benzo[1,3]dioxin-8-yl ester 
• 143465-52-5 Phosphoric acid (1S,2R,3R,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-2-((R)-3-methoxymethoxy-tetradecanoylamino)-cyclohexyl ester diphenyl ester 
• 143465-55-8 (R)-3-Methoxymethoxy-tetradecanoic acid (4aR,6S,7R,8R,8aR)-6-(diphenoxy-phosphoryloxy)-7-((R)-3-methoxymethoxy-tetradecanoylamino)-2,2-dimethyl-hexahydro-benzo[1,3]dioxin-8-yl ester 
• 143465-59-2 Phosphoric acid (2R,4aR,6S,7R,8R,8aR)-7-((R)-3-benzyloxymethoxy-tetradecanoylamino)-8-hydroxy-2-phenyl-hexahydro-benzo[1,3]dioxin-6-yl ester diphenyl ester 

Relevant academic research and scientific papers

Optimized and Scalable Synthesis of Carba-α-d-Glucosamine

An efficient, high-yielding synthesis of carba-α-d-glucosamine is reported. Key features of this optimized route include an innovative protecting group strategy and an unusual, stereoconvergent Ferrier carbocyclization of a hindered substrate. The sequenc

Fluoro-Carba-Sugars are Glycomimetic Activators of the glmS Ribozyme

The glmS ribozyme is a bacterial gene-regulating riboswitch that controls cell wall synthesis, depending on glucosamine-6-phosphate as a cofactor. Due to the presence of this ribozyme in several human pathogen bacteria (e.g., MRSA, VRSA), the glmS ribozyme represents an attractive target for the development of artificial cofactors. The substitution of the ring oxygen in carbohydrates by functionalized methylene groups leads to a new generation of glycomimetics that exploits distinct interaction possibilities with their target structure in biological systems. Herein, we describe the synthesis of mono-fluoro-modified carba variants of α-d-glucosamine and β-l-idosamine. (5aR)-Fluoro-carba-α-d-glucosamine-6-phosphate is a synthetic mimic of the natural ligand of the glmS ribozyme and is capable of effectively addressing its unique self-cleavage mechanism. However, in contrast to what was expected, the activity is significantly decreased compared to its non-fluorinated analog. By combining self-cleavage assays with the Bacillus subtilis and Staphylococcus aureus glmS ribozyme and molecular docking studies, we provide a structure–activity relationship for fluorinated carba-sugars.

Synthesis of the carbon pseudosugar analog of lipid X

A carbocyclic analog (2) with a deactivated pseudo-anomeric phosphate of the lipopolysaccharide biosynthetic intermediate Lipid X (1) was prepared in order to better understand the biological behavior of the parent compound. Two related synthetic routes t

SYNTHETIC METHODS FOR THE PREPARATION OF BASIC D- AND L-PSEUDO-SUGARS. SYNTHESIS OF CARBOCYCLIC ANALOGUES OF N-ACETYL-MURAMYL-L-ALANYL-D-ISOGLUTAMINE (MDP)

Two exocyclic olefins 10 and 22, readily elaborated from D-glucosamine, have been transformed by Ferrier rearrangement reaction into aminocyclohexanones 11, 12 and 23, 24.Reduction of ketone 11 with tri-t-butoxy-aluminium hydride followed by sequential ac