57043-00-2

Basic information

• Product Name: (1RS,2SR)-cispentacin
• Synonyms: (1RS,2SR)-cispentacin
• CAS NO: 57043-00-2
• Molecular Weight: 129.159
• Mol File: 57043-00-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (1RS,2SR)-cispentacin(CAS DataBase Reference)
• NIST Chemistry Reference: (1RS,2SR)-cispentacin(57043-00-2)
• EPA Substance Registry System: (1RS,2SR)-cispentacin(57043-00-2)

Safety Data

• Hazardous Substances Data: 57043-00-2(Hazardous Substances Data)

Upstream product

• 40482-10-8 2-carbamoylcyclopentanecarboxylic acid 
• 1560-11-8 cyclopent-1-enecarboxylic acid 
• 136315-70-3 (±)-cis-2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylic acid 
• 22031-52-3 cis-2-aza-3-oxobicyclo<3.2.0>heptane 
• 1609100-30-2 ethyl cis-2-aminocyclopentane-1-carboxylate 
• 821-41-0 5-Hexen-1-ol 
• 764-59-0 hex-5-en-1-al 
• 4492-47-1 (+/-)-cis-2-(hydroxymethyl)cyclopentylamine 
• 152495-65-3 C₁₃H₁₇NO 
• 6140-65-4 1-cyclopentene-1-carboxaldehyde 

Downstream Products

• 61935-49-7 cis-2-benzyloxycarbonylamino-cyclopentanecarboxylic acid 
• 129169-58-0 (1R,2S)-2-Amino-cyclopentanecarboxylic acid phenylamide 
• 137170-89-9 (1S,2R)-2-((tert-butoxycarbonyl)amino)cyyclopentane-1-carboxylic acid 
• 130981-12-3 (-)-N-(tert-butyloxycarbonyl)-cis-2-aminocyclopentanecarboxylic acid 

Relevant articles and documents

Stereoselective organocatalytic approach to α,β-disubstituted- β-amino acids: A short enantioselective synthesis of cispentacin

α-Branched α,β-unsaturated aldehydes have been tested in the organocatalytic tandem Michael addition/cyclization with N-(benzyloxycarbonyl)hydroxylamine, a reaction which until now has been restricted to α-unsubstituted enals. Starting from cyclopentene-2- carbaldehyde, and using diphenylprolinol trimethylsilyl ether as a chiral amine catalyst, this approach has led to the development of a practical, high yielding (93-98 % overall yield, three steps), and highly enantioselective (up to 98:2 er) route to the cyclic β-amino acid cispentacin, which compares favourably with previously described asymmetric syntheses of this biologically active natural product. When using acyclic α-branched α,β-unsaturated aldehydes as substrates, the reaction yields depend on the substitution pattern of the aldehydes, and mixtures of cis- and trans-isomers are obtained. Nevertheless, this strategy has proved to be successful in some instances, and (3R,4R)-benzyl 3-ethyl-4-methyl-5-oxoisoxazolidin-2-carboxylate could be obtained in 70 % overall yield (two steps) from the reaction of 2-ethylcrotonaldehyde and N-(benzyloxycarbonyl)hydroxylamine under catalysis with diphenylprolinol trimethylsilyl ether, and with high enantiomeric purity (99:1 er). The organocatalytic tandem Michael addition/cyclization of cyclopentene-2-carbaldehyde with N-Cbz-hydroxylamine, using diphenylprolinol TMS ether as a chiral amine catalyst, gives a practical, high yielding, and highly enantioselective route to the cyclic β-amino acid cispentacin. Acyclic α-branched enals give variable results in the same reaction, depending on the substitution pattern. Copyright

A novel preparation of 2-aminocyclopentanecarboxamides

Different syntheses of cis- and trans-2-aminocyclopentanecarboxamides were studied. A convenient and effective method was devised for the preparation of cis-2-aminocyclopentanecarboxamide derivatives starting from the readily available 6-tert-butoxycarbon

Synthesis of racemic and optically active cispentacin (FR109615) using intramolecular nitrone-olefin cycloaddition

Synthesis of racemic and optically active cispentacin ((-)-1) is described. Intramolecular nitrone-olefin cycloaddition of the alkenyl nitrone 7 gave cis-isoxazolidine (±)-8, which was transformed into (±)-1 by sequential reactions involving catalytic hyd