77059-32-6

Upstream product

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

Downstream Products

• 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 
• 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 
• 612493-14-8 6-[methyl 2-deoxy-2-(N-benzyloxycarbonylamino)-D-glucopyranosidyl]diethyl phosphate 
• 612493-18-2 [(1S,2R,3S,4R)-5-(Diethoxy-phosphoryloxy)-2,3,4-trihydroxy-1-hydroxymethyl-pentyl]-carbamic acid benzyl ester 
• 62858-36-0 methyl 2-benzyloxycarbonylamino-6-bromo-2,6-dideoxy-α-D-gluco-pyranoside 
• 17460-45-6 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-alpha-D-glucopyranose 
• 144001-84-3 (S)-2-[(1R,2R)-2-Acetoxy-1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester 
• 144001-85-4 (S)-2-[(1R,2S)-2-Acetoxy-1-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-aziridine-1-carboxylic acid benzyl ester 
• 144001-93-4 Acetic acid (1R,2R,3R)-3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-oxo-1-vinyl-butyl ester 
• 144001-83-2 Acetic acid (1R,2R,3S)-3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-vinyl-butyl 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.

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

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.

Regioselective sulfamoylation at low temperature enables concise syntheses of putative small molecule inhibitors of sulfatases

Regioselective sulfamoylation of primary hydroxyl groups enabled a 5-step synthesis (overall yield 17%) of the first reported small molecule inhibitor of sulfatase-1 and 2, ((2S,3R,4R,5S,6R)-4,5-dihydroxy-2-methoxy-6-((sulfamoyloxy)methyl)tetrahydro-2H-pyran-3-yl)sulfamic acid, which obviated the use of hydroxyl protecting groups and is a marked improvement on the reported 9-step synthesis (overall yield 9%) employing hazardous trifluoromethylsulfonyl azide. The sulfamoylation methodology was used to prepare a range of derivatives of 1, and inhibition data was generated for Sulf-2, ARSA and ARSB.

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

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.

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.