21559-73-9

Upstream product

• 108-93-0 cyclohexanol 
• 1040191-33-0 N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfono-hydrazide 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 21559-74-0 cyclohexyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-glucopyranoside 
• 187738-49-4 cyclohexyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-glucopyranoside 
• 187738-47-2 cyclohexyl 2-acetamido-4,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside 
• 187738-48-3 cyclohexyl 2-acetamido-3,6-tri-O-benzoyl-2-deoxy-α-D-glucopyranoside 
• 7512-17-6 N-Acetyl-D-glucosamine 

Downstream Products

• 624738-78-9 (R)-4-{(S)-2-[(R)-2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-cyclohexyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester 
• 624738-69-8 (R)-4-{(S)-2-[(R)-2-((2S,3R,4R,5S,6R)-3-Acetylamino-2-cyclohexyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester 
• 624738-74-5 cyclohexyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-3-O-[(R)-1-carboxyethyl]-α-D-glucopyranoside 
• 187738-42-7 N-((2S,3R,4R,5S,6R)-2-Cyclohexyloxy-4,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-3-yl)-N-methyl-acetamide 
• 499104-65-3 N-((3R,4R,5S,6R)-2-Cyclohexyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide 
• 509086-48-0 cyclohexyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside 

Relevant academic research and scientific papers

Protecting group free glycosidations using p-toluenesulfonohydrazide donors

(Figure Presented) N-Glycopyranosylsulfonohydrazides are introduced as glycosyl donors for protecting group free synthesis of O-glycosides, glycosyl azides, and oxazolines. Mono- and disaccharides containing a reducing terminal N-acelylglucosamine residue were condensed with p-toluenesulfonylhydrazide to give the desired β-D-pyranose donors. These donors can be activated with NBS and then glycosidated with the desired alcohol or transformed to the oxazoline or glycosyl azide.

N-Acetylmuramyl-L-Alanyl-D-Isoglutamine Glycosides: Effect of Glycoside Bond Configuration and Aglycone on Biological Activity

Hexyl, octyl, and cyclohexyl β-glycosides and heptyl and cyclohexyl α-glycosides of muramyl dipeptide (MDP) were synthesized. Tests in vitro and in vivo revealed lower immunostimulating activities of MDP α-glycosides in comparison with the corresponding β-glycosides and MDP itself. In the case of alkyl β-glycosides, differences in hydrocarbon chain lengths (C4-C8) and in aglycone (aliphatic chain and aliphatic or aromatic ring) exerted no substantial effect on the immunostimulating activity.

The synthesis of α-glycosides of methyl N-acetylmuramyl-L-alanyl-D-isoglutaminate

1-Heptanol, cyclohexanol, and cholesterol were glycosylated with α-glucosaminylchloride peracetate in the presence of HgI2 at 80-90°C to the corresponding peracetylated α-glycosides of N-acetylglucosamine. Successive Zemplen deacetylation, benz

Mechanism of anomerization of cyclohexyl 2-deoxy-3,4,6-tri-O-methyl-2-(N-methylacetamido)-α- and β-D-hexopyranosides under reductive-cleavage conditions

The fully methylated cyclohexyl glycosides of 2-acetamido-2-deoxy-α- and β-D-hexopyranoses having the gluco, manno, and galacto configurations were each subjected to reductive-cleavage conditions using one of three promoters, namely trimethylsilyl, triflu