71204-43-8

Upstream product

• 79974-79-1 benzyl 2,3-anhydro-β-L-erythropentopyranosid-4-ulose 
• 108292-99-5 benzyl 2,3-anhydro-4-O-formyl-α-D-lyxopyranoside 
• 87-72-9 L-(+)-arabinose 
• 100-51-6 benzyl alcohol 
• 18403-22-0 (3aS,6S,7R,7aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol 
• 7473-38-3 benzyl β-L-arabinopyranoside 
• 68753-33-3 (+)-benzyl-3,4-O-isopropyliden-2-O-(p-toluolsulfonyl)-β-L-arabinopyranoside 
• 26524-58-3 (+)-benzyl-2-O-(p-toluolsulfonyl)-β-L-arabinopyranoside 
• 71204-45-0 benzyl 2,3-anhydro-4-O-trifluoromethanesulfonyl-β-L-ribopyranoside 
• 7625-53-8 L-alanine methylester 
• 2666-93-5 L-Leucine methyl ester 
• 2577-90-4 L-phenylalanine methyl ester 
• 10332-17-9 L-methionine methyl ester 
• 2577-48-2 L-proline methyl ester 

Downstream Products

• 71204-46-1 benzyl 2,3-anhydro-4-O-(trifluoromethylsulfonyl)-α-D-lyxopyranoside 
• 79974-80-4 Benzyl-2,3-anhydro-4-O-benzyl-α-D-lyxopyranosid 
• 115983-57-8 benzyl 2,3-anhydro-4-O-(tert-butyldimethylsilyl)-α-D-lyxopyranoside 
• 87668-67-5 benzyl 3-chloro-3-deoxy-α-D-arabinopyranoside 
• 141520-76-5 benzyl 3-diethylamino-3-deoxy-α-D-arabinopyranoside 
• 163493-64-9 Benzyl-3-cyano-3-deoxy-α-D-arabinopyranoside 
• 165269-06-7 Benzoyl-carbamic acid (1S,2S,5R,6S)-2-benzyloxy-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester 
• 142048-15-5 benzyl 2,3-anhydro-4-desoxy-4-pyridinium-β-L-ribopyranoside 
• 65518-85-6 benzyl-2,3-anhydro-4-amino-4-desoxy-β-L-ribopyranoside 
• 93125-74-7 Benzyl 2,3-anhydro-β-L-ribopyranoside 4-nitrate 
• 115983-65-8 benzyl 2-deoxy-2-C-methyl-4-O-(tert-butyldimethylsilyl)-α-D-xylonopyranoside 
• 115983-64-7 benzyl 3-deoxy-3-C-methyl-4-O-(tert-butyldimethylsilyl)-α-D-arabinopyranoside 
• 115983-71-6 Acetic acid (2S,3R,4R,5R)-2-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-tetrahydro-pyran-4-yl ester 
• 79974-82-6 Benzyl-3-azido-4-O-benzyl-3-desoxy-2-O-methylsulfonyl-α-D-arabinopyranosid 

Relevant academic research and scientific papers

Synthesis and inhibition properties of a series of pyranose derivatives towards a Zn-metalloproteinase from Saccharomonospora canescens

The Zn-proteinase, isolated from Saccharomonospora canescens (NPS), shares many common features with thermolysin, but considerable differences are also evident, as far as the substrate recognition site is concerned. In substrates of general structure AcylAlaAlaPhe 4NA, this neutral proteinase cleaves only the arylamide bond (non-typical activity of Zn-proteinases), while thermolysin attacks the peptide bond Ala-Phe. Phosphoramidon is a powerful tight binding inhibitor for thermolysin and significantly less specific towards NPS. The Ki-values (65 μM for NPS vs 0.034 μM for thermolysin) differ nearly 2000-folds. This implies significant differences in the specificity of the corresponding subsites. The carbohydrate moiety is supposed to accommodate in the S1-subsite and the series of arabinopyranosides and glucopyranosides (12 compounds), which are assayed as inhibitors in a model system: NPS with SucAlaAlaPhe4NA as a substrate could be considered as mapping the S1-subsite of NPS. Members of the series with an additional ring (3,4-epithio, 3,4-anhydro-derivatives) turned out to be reasonably good competitive inhibitors (Ki ≈ 0.1-0.2 mM are of the same order as the Ki value for phosphoramidon). The structure of these compounds (8, 9, 11 and 12) seems to fit the size of the S1-subsite and due to an appropriately oriented OH-group in addition, to protect the active site Zn2+.

Regio- and Stereoselective Ring Opening of Epoxy Pyranosides with Titanium Isopropoxide Reagents and SmI2: A Straightforward Access to Iododeoxy Sugars

A regioselective synthesis of 3-iodo-3-deoxy sugars is described by trans-diaxial cleavage of the oxirane ring of 2,3-anhydropyranosides with halogenated titanium isopropoxide reagents and samarium iodide.

Synthesis of 3-Amino-3-deoxy Sugars through Intramolecular Carbamate Cyclizations on a Neighbouring Oxirane Ring

Keywords: 3-Amino-3-deoxy Sugars, Triflate Sugars, Carbamates

Regioselective and Stereoselective Oxirane Ring-Openings of 2,3-Anhydropentopyranosides with Some Methyl Group Donating Organometallic Reagents

By the proper choice of methyl group transferring reagents organometallic (Me4AlLi, Me4AlLi/MeLi (1:1), Me2CuLi, Me3Al, Me2Mg) it is possible to selectively introduce a methyl group into the 2- or 3-position via epoxide ring-opening of four easily availab

Efficient High-Yielding Syntheses and NMR Spectroscopic Studies of Some Fluorodeoxy Sugars

Displacement of the triflyl group by fluoride ion in benzyl 2,3-anhydro-4-O-(trifluoromethylsulfonyl)pyranosides 1-3 leads with stereochemical inversion to the 4-fluoro-4-deoxy sugars 4-6, providing a general method for the introduction of fluorine in the

Classical Synthesis of a New Class of Compounds via Coupling of Sugars and Amino Acids

A new class of pharmacologically interesting compounds has been synthesized through a novel SN2 displacement of the CF3SO2 group in benzyl 2,3-anhydro-4-trifluoromethylsulphonyl-α-D-ribopyranoside (1) and its β-L-isomer (2), by a variety of suitably protected naturally occurring amino acids: the reaction pathway also provides an efficient route to benzyl 2,3-anhydro-β-L- and -α-D-lyxopyranosides .

C-4-Triflate Displacement by Azide in 2,3-Anhydro Sugars; a New Way to 4-Amino-4-deoxy Sugars

Displacement of the triflyl by the azido group in benzyl-2,3-anhydro-4-triflyl-α-D-pyranosides 4-6 gives with inversion the benzyl-2,3-anhydro-4-azido-4-deoxypyranosides 7-9.The triflyl group turns out to be a reactive leaving group which can be replaced

Syntheses of 2,3-Diamino-2,3-dideoxypentoses

Nucleophilic ring opening of the aziridino sugar 5 with sodium azide gave compound 6 with arabino-configuration.Similar treatment of 13 gave the xylo-derivative 14.Both products are contrary to the predictions of the Fuerst-Plattner rule. 2,3-Diacetamido-