193808-59-2

Basic information

• Product Name: 4,5-Pyridazinediol,hexahydro-3-methyl-,(3alpha,4beta,5beta)-(9CI)
• Synonyms: 4,5-Pyridazinediol,hexahydro-3-methyl-,(3alpha,4beta,5beta)-(9CI)
• CAS NO: 193808-59-2
• Molecular Formula: C5H12N2O2
• Molecular Weight: 132.16
• Product Categories: PYRIDAZINE
• Mol File: 193808-59-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4,5-Pyridazinediol,hexahydro-3-methyl-,(3alpha,4beta,5beta)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-Pyridazinediol,hexahydro-3-methyl-,(3alpha,4beta,5beta)-(9CI)(193808-59-2)
• EPA Substance Registry System: 4,5-Pyridazinediol,hexahydro-3-methyl-,(3alpha,4beta,5beta)-(9CI)(193808-59-2)

Safety Data

• Hazardous Substances Data: 193808-59-2(Hazardous Substances Data)

Upstream product

• 449146-84-3 (3R,4R,5R)-1,2-diacetyl-4,5-dibenzyloxy-3-hydroxymethylhexahydropyridazine 
• 449146-91-2 (3S,4R,5R)-1,2-diacetyl-4,5-dibenzyloxy-3-chloromethylhexahydropyridazine 
• 449146-92-3 (3R,4R,5R)-1,2-diacetyl-4,5-dibenzyloxy-3-methylhexahydropyridazine 
• 449146-80-9 1-(2-tert-butyloxycarbonylhydrazino)-1,5-dideoxy-2,3-di-O-isopropylidene-D-ribitol 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 449146-82-1 (3S,4R,5S)-1-acetyl-4,5-isopropylidenedioxy-3-methylhexahydropyridazine 
• 10316-50-4 (+/-)-2-methyl-8-phenyl-1,6,8-triazabicyclo<4.3.0>non-3-ene-7,9-dione 
• 449146-81-0 1-(1-acetyl-2-tert-butoxycarbonylhydrazino)-1,5-dideoxy-2,3-di-O-isopropylidene-4-O-methylsulfonyl-D-ribitol 
• 950182-24-8 (3aR,6R,6aR)-2,2-dimethyl-6-(tosyloxymethyl)-tetrahydro-2H-furo[3,4-d]-1,3-dioxol-4-ol 
• 158112-53-9 (3aR,6R,6aR)-2,2,6-trimethyltetrahydro-2H-furo(3,4-d)(1,3)dioxol-4-ol 

Relevant articles and documents

Synthesis and investigation of L-fuco- and D-glucurono-azafagomine

The new azasugars (3S,4R,5S)-4,5-dihydroxy-3-methylhexahydropyridazine (3, azafucofagomine) and (3S,4R,5R)4,5-dihydroxyhexahydropyridazine-3-carboxylic acid (4, azaglucuronofagomine) were synthesised. Azafucofagomine (3) was made from D-ribose in ten step

1-Azafagomine: A hydroxyhexahydropyridazine that potently inhibits enzymatic glycoside cleavage

(3,4-trans-4,5-trans)-4,5-dihydroxy-3-hydroxymethylhexahydropyridazine (16) was synthesized in four steps from 2,4-pentadienol (22) and 4-phenyltriazolin-3,5-dione (18) in an overall yield of 32%. In the first step a Diels Alder reaction between 18 and 22 gave (±)-2-hydroxymethyl-8-phenyl-1,6,8-triazabicyclo[4.3.0]non-3-ene-7,9-dione (23c) in 88% yield. Epoxidation of 23c with trifluoromethyl(methyl)dioxirane, generated in situ, gave the trans epoxide 24c in 62% yield. Hydrolysis of the epoxide with perchloric acid gave stereoselectively (2,3-trans-3,4-trans)-3,4-dihydroxy-2-hydroxymethyl-8-phenyl-1,6,8-triazabicy clo[4.3.0]-nonane-7,9-dione (26) in 73% yield. In the fourth and final step, hydrazinolysis of 26 gave 16 in 84% yield. Pyridazine 16 was found to be a potent inhibitor of χ-and β-glucosidase, isomaltase and glycogen phosphorylase, while galactosidases and χ-mannosidase were not inhibited. The inhibition of β-glucosidase is independent of pH, and was found to be due to unprotonated 16.