77059-32-6

Basic information

• Product Name: 2-N-CARBOBENZYLOXY-2-DEOXY-D-GLUCOSAMINE
• CAS NO: 77059-32-6
• Molecular Formula: C₁₄H₁₉NO₇
• Molecular Weight: 313.30316
• Mol File: 77059-32-6.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 606.0±55.0 °C(Predicted)
• Appearance: /
• Density: 1.47±0.1 g/cm3(Predicted)
• PKA: 10.45±0.70(Predicted)
• CAS DataBase Reference: 2-N-CARBOBENZYLOXY-2-DEOXY-D-GLUCOSAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-N-CARBOBENZYLOXY-2-DEOXY-D-GLUCOSAMINE(77059-32-6)
• EPA Substance Registry System: 2-N-CARBOBENZYLOXY-2-DEOXY-D-GLUCOSAMINE(77059-32-6)

Safety Data

• Hazardous Substances Data: 77059-32-6(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 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 
• 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 
• 35946-66-8 2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate 
• 909257-20-1 methyl-(2-benzyloxycarbonylamino-O³-methyl-2-deoxy-α-D-glucopyranoside) 
• 206126-52-5 ((4aR,6S,7R,8R,8aS)-6,8-Dimethoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid benzyl ester 
• 206126-53-6 (2S,3S,4R,5R,6S)-5-Benzyloxycarbonylamino-3-hydroxy-4,6-dimethoxy-tetrahydro-pyran-2-carboxylic acid 
• 61348-62-7 methyl 2-[(benzyloxycarbonyl)amino]-2-deoxy-4,6-isopropylidene-α-D-glucopyranoside 
• 4704-17-0 benzyl ((2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3-yl)carbamate 
• 4704-15-8 ((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester 
• 1350556-07-8 methyl 2-benzyloxycarbonylamino-2-deoxy-3-O-methoxycarbonyl-α-D-glucopyranoside 
• 1350556-10-3 methyl 2-benzyloxycarbonylamino-2-deoxy-4-O-mesyl-3-O-methoxycarbonyl-α-D-glucopyranoside 
• 1350556-11-4 methyl 2-benzyloxycarbonylamino-2-deoxy-3-O-methoxycarbonyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside 

Relevant articles and documents

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.