40519-00-4

Upstream product

• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 119970-97-7 (+)-5-O-(p-Toluolsulfonyl)-D-ribonsaeure-γ-lacton 
• 183889-10-3 4,5-anhydro-2,3-O-isopropylidene-D-ribonic acid benzyl ester 
• 120623-92-9 (3aS,6R,6aR)-6-Hydroxy-2,2-dimethyl-6-phenyl-tetrahydro-cyclopenta[1,3]dioxol-4-one 
• 120623-93-0 (3aS,6aS)-2,2-Dimethyl-6-phenyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one 
• 23735-43-5 (S)-1-O-tosyl-2,3-O-isopropylideneglycerol 
• 50765-70-3 (S)-1-tosyloxy-2,3-propanediol 
• 152006-17-2 2,3-O-isopropylidene-L-lyxono-1,4-lactone 
• 134746-44-4 N-Benzyl-5-amino-4-O-benzyl-5-deoxy-2,3-isopropylidene-D-ribono-1,5-lactam 
• 158112-55-1 5-O-deoxy-D-ribofuranose 

Relevant academic research and scientific papers

Enantioselective total synthesis of the phytotoxic lactone herbarumin I

A concise total synthesis of the potent herbicide herbarumin I (1) is presented based on an (E)-selective RCM reaction forging the 10-membered ring of this macrolide.

One-pot tandem strecker reaction and iminocyclisations: Syntheses of trihydroxypiperidine α-iminonitriles

Unbranched, and α- and β-methyl-branched, trihydroxypiperidine α-iminonitriles have been obtained in a single step from protected 5-O-tosylate pentoses. This reaction comprises a one-pot tandem Strecker reaction and iminocyclisation. These trihydroxypiper

Synthesis of analogues of salacinol containing a carboxylate inner salt and their inhibitory activities against human maltase glucoamylase

The syntheses of analogues of the naturally occurring glycosidase inhibitor, salacinol, containing a carboxylate inner salt are described. Salacinol is a sulfonium ion with an internal sulfate counterion. The synthetic strategy relies on the nucleophilic

GLYCOSIDASE INHIBITORS AND METHODS OF SYNTHESIZING SAME

The compounds of the present invention relate to chain-extended and chain-modified analogues of salacinol, including embodiments where the sulfate moiety has been substituted with a carboxylate or phosphate moiety. In other embodiments the sulfate moiety has been shifted by one carbon atom in the zwitterionic structure. In another embodiment the polyhydroxylated side chain may be replaced with a lipophilic alkyl chain and a suitable counterion. The invention also encompasses methods for synthesizing the salacinol analogues and using the analogues for enzyme inhibition applications.

Total syntheses of the phytotoxic lactones herbarumin I and II and a synthesis-based solution of the pinolidoxin puzzle

A concise approach to a family of potent herbicidal 10-membered lactones is described on the basis of ring-closing metathesis (RCM) as the key step for the formation of the medium-sized ring. This includes the first total syntheses of herbarumin I (1) and

Nδ-(5-Hydroxy-4,6-dimethylpyrimidine-2-yl)-L-ornithine, a novel methylglyoxal - Arginine modification in beer

Nδ-(5-Hydroxy-4,6-dimethylpyrimidine-2-yl)-L-ornithine, or Argpyrimidine, was identified and quantified in beer by high-performance liquid chromatography (HPLC) and coupled gas chromatography-mass spectrometry (HRGC-MS). This novel fluorescent

Organotransition Metal Modified Sugars, Part 10. Chromium Iminoglycosylidenes: Synthesis and Application to Photoinduced C-Glycosidation

The iminoglycosylidene complexes 3a,b, 9, and 16a,b are conveniently prepared from the sugar lactams 2a,b, 8, and 15a,b by reaction with K2Cr(CO)5 and subsequent deoxygenation with trimethylsilyl chloride (TMSCl). The Cr(CO)5-stabilized carbene moiety of the imino-D-ribo-pyranosylidene complexes 9 and 16a,b has been exploited in the photoinduced generation of ketene-like species on irradiation with UV light. These intermediates were trapped with methanol to produce the methyl 2,6-imino-D-allonates 10 and 17a,b. The C-glycosidation is β-selective and has been applied futher to the preparation of the galactosyl 2,6-imino-D-allonate 19. Solvent effects suggest that the diastereoselectivity originates in the chromium fragment, which shields the re face of the proposed ketene intermediate. - Keywords: chromium; carbene complexes; glycosides; iminosugars; photolysis

First synthesis of aldopentono-1,4-thiolactones

A convenient synthesis of enantiomerically pure aldopentono-1,4- thiolactones is described. Thus, 4-thio-D-ribono-1,4-lactone (12) has been prepared from D-gulono-1,4-lactone (1), via its 2,3-O-isopropylidene derivative 3. The 5,6-glycol system of 3 was o

TOTAL SYNTHESIS OF (+)-ELDANOLIDE FROM D-RIBONOLACTONE

A new and useful synthesis of (+)-Eldanolide is reported, D-ribonolactone being used as a chiral starting product.

SYNTHESIS OF EIGHT STEREOISOMERIC 5-(ADENIN-9-YL)-2,3,4-TRIHYDROXYPENTANOIC ACIDS

Condensation of 5-O-p-toluenesulfonyl-2,3-O-isopropylidene-D-ribonolactone (XIIIb) with sodium salt of adenine afforded compound XIV which on alkaline, followed by acid, hydrolysis gave the (2R,3R,4R)-isomer V.The (2S,3S,4S)-isomer VIII was prepared analogously from the L-ribonolactone derivative XVb via the adenine derivative XVI. Compound XVIIc was transformed by reaction with adenine into 6-(adenin-9-yl)-6-deoxy-D-glucose (XIX); similarly, 6-(adenin-9-yl)-6-deoxy-D-mannose (XXI) was prepared from the protected D-mannofuranoside XX.Oxidation of compounds XIX and XXI in alkaline medium afforded the (2S,3R,4R)-isomer VI, 1,2:3,4-Di-O-isopropylidene-D-galactopyranose (XXIIa) was transformed into 6-(adenin-9-yl)-6-deoxy-D-galactose (XXIIIb) which was oxidatively cleaved to give the (2S,3S,4R)-isomer VII.Methyl 5,6-di-O-methanesulfonyl-2,3-O-isopropylidene-D-mannofuranoside (XXVIb) was transformed into the reactive L-gulofuranoside derivative XXVIIe which on condensation with adenine and oxidative cleavage gave the (2S,3R,4S)-isomer IX.The (2R,3S,4R)-isomer XI was prepared analogously from the D-gulofuranose derivative XXXIb.Starting from L-mannose, the (2R,3S,3S)-derivative X was prepared via the 6-(adenin-9-yl)-6-deoxy-L-mannofuranoside derivative XXXc.Methyl 5-O-p-toluenesulfonyl-2,3-O-isopropylidene-L-lyxofuranoside XXXVb was transformed into 5-(adenin-9-yl)-5-deoxy-2,3-O-isopropylidene-L-lyxofuranose (XXXVII) which was oxidized to the lactone XXXVIII; this compound on successive alkaline and acid hydrolysis afforded the (2R,3R,4S)-isomer XII.