7474-40-0

Usage

Derivative of hexopyranose

Hexopyranose is a type of carbohydrate or sugar molecule 2-{[(benzyloxy)carbonyl]amino}-2-deoxyhexopyranose is derived from hexopyranose, which is a sugar molecule, by adding various functional groups.

Benzyl group attachment

Attached to the oxygen atom of the carbonyl group The benzyl group, a phenyl ring with a methyl group, is connected to the oxygen atom in the carbonyl group (C=O) of the compound.

Amino group attachment

Attached to the carbon atom of the hexopyranose ring An amino group (NH2) is connected to a carbon atom in the hexopyranose ring, contributing to the compound's reactivity and potential applications.

Useful for chemical reactions and synthetic purposes

The presence of the benzyloxy and amino groups These functional groups make the compound versatile and valuable for various chemical reactions and synthetic applications, such as the synthesis of complex molecules and pharmaceuticals.

Importance in organic chemistry

Synthesis of complex molecules and pharmaceuticals 2-[(benzyloxy)carbonyl]amino-2-deoxyhexopyranose plays a significant role in the field of organic chemistry, particularly in the synthesis of complex molecules and pharmaceuticals, due to its unique structure and functional groups.

Upstream product

• 90-76-6 2-deoxy-2-amino glucose 
• 501-53-1 benzyl chloroformate 
• 4710-95-6 D-mannosamine hydrochloride 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 14131-62-5 D-glucosamine hydrochloride 

Downstream Products

• 57089-81-3 methyl 2-benzyloxycarbonylamino-2-deoxy-α/β-D-glucopyranoside 
• 4704-15-8 ((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester 
• 121230-19-1 2-benzyloxycarbonylamino-2-deoxy-4,6-O-ethylidene-α,β-D-glucose 
• 73707-69-4 2-(benzyloxycarbonylamino)-2-deoxy-3,4:5,6-di-O-isopropylidene-aldehydo-D-glucose dibenzyl acetal 
• 73707-69-4 [(R)-2,2-Bis-benzyloxy-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl]-carbamic acid benzyl ester 
• 35946-66-8 2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate 
• 82264-19-5 1,3,4,6-tetra-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside 
• 5348-99-2 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(benzyloxycarbonyl)amino-α/β-D-glucopyranoside 
• 73707-67-2 2-(benzyloxycarbonylamino)-2-deoxy-3,4:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 
• 73707-67-2 [(R)-2,2-Dimethoxy-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl]-carbamic acid benzyl ester 
• 2862-10-4 benzyl-(2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside) 
• 83663-03-0 benzyl ((2S,3R,4R,5S,6R)-2-(allyloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate 
• 315229-38-0 ((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexylamino)-acetic acid methyl ester 
• 315229-51-7 (S)-2-((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexylamino)-6-tert-butoxycarbonylamino-hexanoic acid methyl ester 

Relevant academic research and scientific papers

Protected N-Acetyl Muramic Acid Probes Improve Bacterial Peptidoglycan Incorporation via Metabolic Labeling

Metabolic glycan probes have emerged as an excellent tool to investigate vital questions in biology. Recently, methodology to incorporate metabolic bacterial glycan probes into the cell wall of a variety of bacterial species has been developed. In order to improve this method, a scalable synthesis of the peptidoglycan precursors is developed here, allowing for access to essential peptidoglycan immunological fragments and cell wall building blocks. The question was asked if masking polar groups of the glycan probe would increase overall incorporation, a common strategy exploited in mammalian glycobiology. Here, we show, through cellular assays, that E. coli do not utilize peracetylated peptidoglycan substrates but do employ methyl esters. The 10-fold improvement of probe utilization indicates that (i) masking the carboxylic acid is favorable for transport and (ii) bacterial esterases are capable of removing the methyl ester for use in peptidoglycan biosynthesis. This investigation advances bacterial cell wall biology, offering a prescription on how to best deliver and utilize bacterial metabolic glycan probes.

Asymmetric Synthesis and Biological Activities of Pactamycin-Inspired Aminocyclopentitols

Pactamycin is a structurally unique aminocyclitol antibiotic with broad-spectrum cell growth inhibitory activity. To explore the bountiful activity of the aminocyclitol core of pactamycin, an efficient, modular, and asymmetric synthesis of aminocyclopentitols resembling the pactamycin pharmacophore has been developed employing a SmI2-mediated imino-pinacol coupling strategy. Two of the compounds exhibited antitumor activity against A375 melanoma cells.

AMPHETAMINE PRODRUGS

The present invention relates to amphetamine prodrugs which provide colonic release of amphetamine.

A METHOD FOR OBTAINING CRYSTALLINE LACTO-N-TETRAOSE AND LACTO-N-NEOTETRAOSE PRECURSORS AND MIXTURES THEREOF

A mixture of, preferably a mixture consisting essentially of, an lacto-N-tetraose (LNT) precursor (1) and an lacto-N-neotetraose (LNnT) precursor (2), (formula 1, 2), where R is a group removable by hydrogenolysis and R3 is either a group remov

Automated solid-phase synthesis of hyaluronan oligosaccharides

Well-defined fragments of hyaluronic acid (HA) have been obtained through a fully automated solid-phase oligosaccharide synthesis. Disaccharide building blocks, featuring a disarmed glucuronic acid donor moiety and a di-tert-butylsilylidene-protected gluc

High-efficiency synthesis of chitooligosaccharides

The solid-phase synthesis of chitooligosaccharides is described. After the NHCbz trichloroacetimidate donors 6 and 14 were synthesized; solid-phase synthesis was performed using the Wang resin as support. The illustrated tetra-Nacetyl- chitotetraose 1 was

Solid-phase synthesis of di-N-acetyl-β-chitobiosyl allosamizoline

The solid-phase synthesis of di-N-acetyl-β-chitobiosyl allosamizoline 2 was reported. After the 6-O-benzyl allosamizoline 16, NHCbz trichloroacetimidate donors 7, and 14 were synthesized; solid-phase synthesis was performed using the Wang resin as support. The target di-N-acetyl-β- chitobiosyl allosamizoline 2 was obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively.

Solid-phase synthesis of Di-N-Acetyl-β-chitobiosyl NAG-thiazoline

The solid-phase synthesis of di-N-acetyl-β-chitobiosyl NAG (N-acetyl D-glucosamine)-thiazoline 3 was reported. After the 6-O-benzyl NAG-thiazoline 9, NHCbz trichloroacetimidate donors 14, and 21 were synthesized, and solid-phase synthesis was performed using the Wang resin as support. The target di-N-acetyl-β-chitobiosyl NAGthiazoline 3 was obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively. donors, Wang resin, Glycosylation reactions.

Hybrid aminoglycoside antibiotics via tsuji palladium-catalyzed allylic deoxygenation

Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an R,β-unsaturated 6′- aldehyde and an allylic 3′-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol % Pd2(dba)3 and Bu3P granted access to a novel series of 3′,4′-dideoxy- 4′,5′-dehydro ring A hybrids. The neomycin-sisomicin hybrid exhibited superior in vitro antibacterial activity to the parent compound neomycin.

Synthesis of D-glucosamine-modified benzo[d][1,2]selenazol-3-(2H)-one derivatives

A new class of organoselenium-saccharide derivatives, 2-amino-2-deoxy - D-glucose-modified benzo[d][1,2]selenazol-3-(2H)-one derivatives, has been synthesized via the cyclization reaction of 2-(chloroseleno)benzoyl chloride and O-protected D-glucosamine derivatives. An efficient synthetic method for the preparation of this type of compounds was developed. It has been found that acetone can react with the chloroseleno group under basic conditions, and organoselenium-saccharide derivatives with free hydroxy groups were obtained only when the OH-1 group of the saccharide was protected. Copyright Taylor & Francis Group, LLC.