21559-72-8

Upstream product

• 21588-60-3 cyclohexyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside 
• 117177-19-2 2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline 
• 108-93-0 cyclohexanol 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 1040191-33-0 N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfono-hydrazide 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 257294-52-3 cyclohexyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 851771-55-6 cyclohexyl 2-deoxy-2-phthalimido-β-D-glucopyranoside 

Downstream Products

• 175469-67-7 cyclohexyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 
• 187738-43-8 N-((2R,3R,4R,5S,6R)-2-Cyclohexyloxy-4,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-3-yl)-N-methyl-acetamide 
• 197574-97-3 N-((4aR,6R,7R,8R,8aS)-6-Cyclohexyloxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide 
• 211567-23-6 cyclohexyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 824396-38-5 cyclohexyl 2-acetamido-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside 
• 824396-44-3 cyclohexyl 2-acetamido-2-deoxy-(R)-4,6-O-(E-2-methyl-3-phenyl-2-propenylidene)-β-D-glucopyranoside 
• 824396-59-0 1-[(3aR,4R,5aR,8R,9aS,9bR)-4-Cyclohexyloxy-8-((E)-styryl)-hexahydro-1,5,7,9-tetraoxa-3-aza-cyclopenta[a]naphthalen-3-yl]-ethanone 
• 824396-60-3 cyclohexyl 2-acetamido-3-O-acetyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside 
• 824396-52-3 cyclohexyl 2-acetamido-3-O-benzyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside 
• 824396-54-5 cyclohexyl 2-acetamido-3-O-benzyl-2-deoxy-(R)-4,6-O-(E-2-methyl-3-phenyl-2-propenylidene)-β-D-glucopyranoside 
• 824396-57-8 N-[6-cyclohexyloxy-8-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yloxy)-2-styryl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 

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.

Facile approach to 2-acetamido-2-deoxy-β-D-glucopyranosides via a furanosyl oxazoline

(Chemical Equation Presented) A concise and convenient route that may be easily scaled is reported for the preparation of unprotected β-glucopyranosides of N-acetyl-D-glucosamine. Reaction of a wide variety of alcohols with a reactive, readily prepared furanosyl oxazoline under acidic conditions affords the corresponding β-D-glucopyranosides in good to high yields. Primary alcohols gave only β-D-glucopyranosides. A mechanism is proposed for this transformation.

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.

Chemical synthesis of N-acetylglucosamine derivatives and their use as glycosyl acceptors by the Mesorhizobium loti chitin oligosaccharide synthase NodC

Rhizobial bacteria synthesize lipo-chitin oligosaccharide signal molecules (Nod factors) that are essential for the formation of symbiotic organs on the roots of host plants, a process known as nodulation. Biosynthesis of the chitin oligosaccharide moiety

Alkylating agents from sugars. Cyclophosphamides derived from 2-amino- 2-deoxy-D-allose

Cyclophosphamides derived from alkyl 2-amino-4,6-O-benzylidene-2-deoxy- β-D-allopyranosides have been synthesized with good yield by treatment of the corresponding 2-amino-2-deoxy-D-allose derivatives with bis(2- chloroethyl)phosphoramide dichloride. The ring-forming reaction took place with very high diastereoselectivity. Subsequent hydrogenolysis gave excellent yields of cyclophosphamides derived from alkyl 2-amino-2-deoxy-β-D- allopyranosides, with hydrophilicity greater than that of the precursors. The starting material was easily available from 2-acetamido-2-deoxy-D-glucose.

Synthesis of hydrophobic derivatives of muramyldipeptides

Methyl esters of the cyclohexyl-, phenethyl-, (2-naphthyl)methyl-, and 2′-(1-naphthyl)ethyl β-glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine have been synthesized. The corresponding glycosides of N-acetylglucosamine were obtained by glycosylating the alcohols with the peracetate of α-glucosaminyl chloride in the presence of HgI2, followed by deacetylation. Subsequent benzylidenation and alkylation with α-L-chloropropionic acid led to glycosylmuramic acids, the condensation of which with the dipeptide and final debenzylidenation gave the desired glycopeptides.

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

EXPEDITIOUS SYNTHESIS OF A TRISUBSTRATE ANALOGUE FOR α(1->3)FUCOSYLTRANSFERASE

The synthesis of cyclohexyl 2-acetamido-2-deoxy-3-O--α-L-fucopyranosyl)-β-D-glucopyranoside (1), a potential inhibitor of α(1->3)fucosyltransferases, is described.Target compound 1 was assembled via fucosylation of