CAS 229613-93-8

methyl (3aR,4R,6S,6aS)-4-((tert-butoxycarbonyl)amino)-3-(pentan-3-yl)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isoxazole-6-carboxylate

Codes: PERA-005

Application context (from source-drug indications)

Influenza virus infectionPeramivir HydrateInfluenza A virus infectionPeramivir HydrateInfluenza B virus infectionPeramivir HydrateNasal congestionPeramivir HydrateFeverPeramivir HydrateCoughPeramivir Hydrate

Source drugs (routes using this intermediate)

Drug	Tier	Expiry
Peramivir Hydrate	Tier C — Watch / trade	-

Position in synthesis routes (up/downstream chain)

Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.

Peramivir HydrateOriginator routesteps: 7total yield: 1.22 g

(1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-one→methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate→methyl (1S,4R)-4-((tert-butoxycarbonyl)amino)cyclopent-2-ene-1-carboxylate→3-(nitromethyl)pentane→methyl (3aR,4R,6S,6aS)-4-((tert-butoxycarbonyl)amino)-3-(pentan-3-yl)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isoxazole-6-carboxylate→methyl (1S,2S,3S,4R)-3-((S)-1-amino-2-ethylbutyl)-4-((tert-butoxycarbonyl)amino)-2-hydroxycyclopentane-1-carboxylate→methyl (1S,2S,3R,4R)-3-((S)-1-acetamido-2-ethylbutyl)-4-((tert-butoxycarbonyl)amino)-2-hydroxycyclopentane-1-carboxylate→methyl (1S,2S,3R,4R)-3-((S)-1-acetamido-2-ethylbutyl)-4-amino-2-hydroxycyclopentane-1-carboxylate→1H-pyrazole-1-carboximidamide hydrochloride

Peramivir HydrateOptimised routesteps: 7total yield: 0.91 g

(1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-one→methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate→methyl (1S,4R)-4-((tert-butoxycarbonyl)amino)cyclopent-2-ene-1-carboxylate→methyl (3aR,4R,6S,6aS)-4-((tert-butoxycarbonyl)amino)-3-(pentan-3-yl)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isoxazole-6-carboxylate→methyl (1S,2S,3S,4R)-3-((S)-1-amino-2-ethylbutyl)-4-((tert-butoxycarbonyl)amino)-2-hydroxycyclopentane-1-carboxylate→methyl (1S,2S,3R,4R)-3-((S)-1-acetamido-2-ethylbutyl)-4-((tert-butoxycarbonyl)amino)-2-hydroxycyclopentane-1-carboxylate→(E)-2-ethylbutanal oxime→methyl (1S,2S,3R,4R)-3-((S)-1-acetamido-2-ethylbutyl)-4-amino-2-hydroxycyclopentane-1-carboxylate hydrochloride→carbamimidic chloride hydrochloride

Peramivir HydrateOptimised routesteps: 6total yield: 49.8 g

methyl (1S,4R)-4-((tert-butoxycarbonyl)amino)cyclopent-2-ene-1-carboxylate→methyl (3aR,4R,6S,6aS)-4-((tert-butoxycarbonyl)amino)-3-(pentan-3-yl)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isoxazole-6-carboxylate→2-azabicyclo[2.2.1]hept-5-en-3-one→methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate (2R,3R)-2,3-dihydroxysuccinate→(Z)-2-ethyl-N-hydroxybutanimidoyl chloride→(3aR,4R,6S,6aS)-4-((tert-butoxycarbonyl)amino)-3-(pentan-3-yl)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isoxazole-6-carboxylic acid→methyl (1S,2S,3S,4R)-3-((S)-1-aminoethyl)-4-((tert-butoxycarbonyl)amino)-2-hydroxycyclopentane-1-carboxylate

Peramivir HydrateOptimised routesteps: 7total yield: /

(1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-one→methyl (1S,4R)-4-((tert-butoxycarbonyl)amino)cyclopent-2-ene-1-carboxylate→3-(nitromethyl)pentane→methyl (3aR,4R,6S,6aS)-4-((tert-butoxycarbonyl)amino)-3-(pentan-3-yl)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isoxazole-6-carboxylate→methyl (1S,2S,3R,4R)-3-((S)-1-acetamido-2-ethylbutyl)-4-((tert-butoxycarbonyl)amino)-2-hydroxycyclopentane-1-carboxylate→methyl (1S,2S,3R,4R)-3-((S)-1-acetamido-2-ethylbutyl)-4-amino-2-hydroxycyclopentane-1-carboxylate→ tert-butyl N-[[(2-methylpropan-2-yl)oxycarbonylamino]-methylsulfanylmethylidene]carbamate→methyl (1S,2S,3R,4R)-3-((S)-1-acetamido-2-ethylbutyl)-4-((Z)-2,3-bis(tert-butoxycarbonyl)guanidino)-2-hydroxycyclopentane-1-carboxylate→(1S,2S,3R,4R)-3-((S)-1-acetamido-2-ethylbutyl)-4-((Z)-2,3-bis(tert-butoxycarbonyl)guanidino)-2-hydroxycyclopentane-1-carboxylic acid

Intermediates available on this site

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Supplier	Product	Price band	MOQ	Lead time	Qualifications	Action
Qualified Partner — East China API Works	(3aR,4R,6S,6aS)-4-[[(1,1-DiMethylethoxy)carbonyl]aMino]-3-(1-ethylpropyl)-3a,5,6,6a-tetrahydro-4H-cyclopent[d]isoxazole-6-carboxylic Acid Methyl Ester Pharmaceutical Intermediates	On request	On request	On request	—

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