(1S,2R,3R,4R)-3-[(1S)-1-acetamido-2-ethyl-butyl]-4-(diaminomethylideneamino)-2-hydroxy-cyclopentane-1-carboxylic acid

Base Information

• Chemical Name: (1S,2R,3R,4R)-3-[(1S)-1-acetamido-2-ethyl-butyl]-4-(diaminomethylideneamino)-2-hydroxy-cyclopentane-1-carboxylic acid
• CAS No.: 229614-56-6
• Molecular Formula: C₁₅H₂₈N₄O₄
• Molecular Weight: 328.412
• Mol file: 229614-56-6.mol

Synonyms:Cyclopentanecarboxylicacid, 3-[(1R)-1-(acetylamino)-2-ethylbutyl]-4-[(aminoiminomethyl)amino]-2-hydroxy-,(1R,2R,3S,4S)-rel- (9CI)

Chemical Property of (1S,2R,3R,4R)-3-[(1S)-1-acetamido-2-ethyl-butyl]-4-(diaminomethylideneamino)-2-hydroxy-cyclopentane-1-carboxylic acid

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 148.53000
• Density: 1.39g/cm³
• LogP: 1.44240

Purity/Quality:

97% ^*data from raw suppliers

Rel-(1R,2R,3S,4S)-3-((S)-1-acetamido-2-ethylbutyl)-4-guanidino-2-hydroxycyclopentanecarboxylicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3R,4R)-3-[(1S)-1-acetamido-2-ethyl-butyl]-4-(diaminomethylideneamino)-2-hydroxy-cyclopentane-1-carboxylic acid

There total 29 articles about (1S,2R,3R,4R)-3-[(1S)-1-acetamido-2-ethyl-butyl]-4-(diaminomethylideneamino)-2-hydroxy-cyclopentane-1-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

(+/-)-3-(1-acetylamino-2-ethylbutyl)-4-[{(tert-butoxycarbonylamino)(tert-butoxycarbonylimino)methyl}amino]-2-hydroxycyclopentanecarboxylic acid → (+/-)-3-(1-acetylamino-2-ethylbutyl)-4-[{aminoiminomethyl}amino]-2-hydroxycyclopentanecarboxylic acid (229614-56-6)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/jo034316b

Reference yield: 73.0%

(-)-(1S,2S,3R,4R)-3-[(1S)-1-(Acetylamino)-2-ethylbutyl]-4-({[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)-imino]methyl}amino)-2-hydroxycyclopentanecarboxylic Acid (383910-27-8) → peramivir (229614-55-5,229614-56-6)

Guidance literature:

(-)-(1S,2S,3R,4R)-3-[(1S)-1-(Acetylamino)-2-ethylbutyl]-4-({[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)-imino]methyl}amino)-2-hydroxycyclopentanecarboxylic Acid; With hydrogenchloride; In water; at 0 ℃;

With sodium hydroxide; In water; pH=6 - 7;

Reference yield: 72.0%

(-)-methyl (1S,2S,3R,4R)-3-[(1S)-1-(acetylamino)-2-ethylbutyl]-4-amino-2-hydroxycyclopentanecarboxylate hydrochloride (229614-17-9) + chloroformamidine hydrochloride (29671-92-9) → peramivir (229614-55-5,229614-56-6)

Guidance literature:

(-)-methyl (1S,2S,3R,4R)-3-[(1S)-1-(acetylamino)-2-ethylbutyl]-4-amino-2-hydroxycyclopentanecarboxylate hydrochloride; With sodium hydroxide; In N,N-dimethyl-formamide; at 0 ℃; for 2h;

chloroformamidine hydrochloride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 24.5h;

With sodium hydroxide; In water; N,N-dimethyl-formamide; pH=8.3 - 8.5;

DOI:10.1080/00397911.2012.729279

upstream raw materials:

(1S,2S,3R,4R)-3-(1-Acetylamino-2-ethyl-butyl)-4-guanidino-2-hydroxy-cyclopentanecarboxylic acid methyl ester

C₁₄H₂₅N₂O₄^(1-)*Na⁽¹⁺⁾

2-Ethylbutyraldehyde

(-)-(1S,2S,3R,4R)-3-[(1S)-1-(Acetylamino)-2-ethylbutyl]-4-({[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)-imino]methyl}amino)-2-hydroxycyclopentanecarboxylic Acid