152094-22-9

Upstream product

• 106758-59-2 (2E)-3-(2`,3`,4`,6`-tetra-O-acetyl-Β-D-glucopyranosyloxy)propenal 
• 152094-21-8 (Tributyl-λ⁵-phosphanylidene)-acetic acid benzyl ester 
• 15097-38-8 (carbobenzyloxymethylene)triphenylphosphorane 
• 5437-45-6 Benzyl bromoacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 529474-45-1 (5S,8S)-2-(2-Benzenesulfonyl-ethyl)-1,3-dioxo-8-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-2,3,5,8-tetrahydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-5-carboxylic acid benzyl ester 
• 252040-00-9 (3S,6S)-6-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyridazine-1,2,3-tricarboxylic acid 1,2-di-tert-butyl ester 
• 529474-48-4 2-(2-benzenesulfonyl-ethyl)-1,3-dioxo-2,3,5,8-tetrahydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-5-carboxylic acid benzyl ester 
• 529474-50-8 2-(2-benzenesulfonyl-ethyl)-1,3-dioxo-hexahydro-[1,2,4]triazolo[1,2-a]pyridazine-5-carboxylic acid 
• 252039-93-3 Methyl (3S,6S)-1,2-bis(benzyloxycarbonyl)-1,2,3,6-tetrahydro-6-(2`,3`,4`,6`-tetra-O-acetyl-β-D-glucopyranosyloxy)pyridazine-3-carboxylate 
• 152094-23-0 Benzyl (3S,6S)-1,2-bis(tert-butoxycarbonyl)-1,2,3,6-tetrahydro-6-(2`,3`,4`,6`-tetra-O-acetyl-β-D-glucopyranosyloxy)pyridazine-3-carboxylate 
• 152186-13-5 (3S)-1-(2,4-Dinitrophenyl)-1,2,3,4,5,6-hexahydropyridazine-3-carboxylic acid 
• 138323-08-7 Methyl (3S)-1-(2,4-dinitrophenyl)-1,2,3,4,5,6-hexahydropyridazine-3-carboxylate 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 

Relevant academic research and scientific papers

Asymmetric synthesis and conformational analysis of the two enantiomers of the saturated analog of the potent thrombin inhibitor MOL-376

Asymmetric synthesis of the two enantiomers of a small molecule thrombin inhibitor is described. The key step in the synthesis is the glucose-directed chiral induction in the hetero Diels-Alder cycloaddition step. Conformational analysis indicates that th

Asymmetric synthesis of (3S)-2,3,4,5-tetrahydropyridazine-3-carboxylic acid and its methyl ester 1

Methyl (2E,4E′)-5-(2′,3′,4′,6′-tetra-O-acetyl-p-D- glucopyranosyloxy)penta-2,4-dienoate 16a, assembled by a Wittig condensation of tributyl(methoxycarbonylmethylene)phosphorane 19a and (2E)-3-(2′,3′,4′,6′-tetra-O-acetyl-′- Dglucopyranosyloxy)propenal 20, displays excellent Re-face reactivity towards diethyl azodicarboxylate 15a, bis(2,2,2trichloroethyl) azodicarboxylate 15b, dibenzyl azodicarboxylate 15c, diisopropyl azodicarboxylate 15d and di-tertbutyl azodicarboxylate 15e in thermal hetero-Diels-Alder reactions to give the cycloadducts 17a-e. When subjected to the action of hydrogen over palladium-carbon, the cycloadducts 17a, 17b, 17d and 17e undergo hydrogenation of their olefinic bonds to give the dihydro derivatives 18a, 18b, 18d and 18e; in the case of the cycloadduct 17c, hydrogenolysis of the benzyloxycarbonyl group also occurs to give methyl (35)-2,3,4,5-tetrahydropyridazine-3carboxylate Ib with an ee of 98% and 2,3,4,6-tetra-O-acetyl-′-D-glucopyranose 22. Compound Ib, with an ee of 98%, is also available from the dihydro derivative 18e by the action of trifluoroacetic acid; however, under the acidic conditions, a condensation reaction between the aglycone Ib and the glycone 22 competes to give methyl (35)-2,3,4,5tetrahydro-2-(2′,3′,4′,6′-tetra-0-acetyl- ′-D-glucopyranosyl)pyridazine-3-carboxylate25. Sodium (35)-2,3,4,5-tetrahydropyridazine-3-carboxylate le, with an ee of 99%, is available from the ester Ib by a saponification reaction. The trifluoroacetic acid salt 27, with an ee of 95%, is obtained from benzyl (35,6S)1,2-bis(tert-butoxycarbonyl)-1,2,3,6-tetrahydro-6-(2′,3′, 4′,6′-tetra-O-acetyl-β-D-glucopyranosyIoxy)pyridazine-3- carboxylate 17g by a hydrogenation-trifluoroacetolysis sequence. A hetero-Diels-Alder reaction involving the benzyl pentadienoate 16c and di-tert-butyl azodicarboxylate 15e provides the cycloadduct 17g. The Royal Society of Chemistry 1999.

Asymmetric Synthesis of (3S)-2,3,4,5-Tetrahydropyridazine-3-carboxylic Acid

The title compound 1a is prepared by a two-step sequence from the cycloadduct 5d, derived from di(tert-butyl) azodicarboxylate and the diene 4b by a hetero Diels-Alder reaction.