cas 136315-70-3, CIS-2-(TERT-BUTOXYCARBONYLAMINO)-1-CYCLOPENTANECARBOXYLIC ACID, 98 | Articles data ｜lookchem

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136315-70-3

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Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers
The proposed diastereoisomers (1 a–d) together with their C8′-epimers (1 e–h) of amipurimycin, a unique antifungal peptidyl nucleoside antibiotic, have been synthesized for the first time. The synthetic approach is efficient and stereodivergent, and features a stereoselective aldol condensation to build the branched C9 sugar amino acid skeleton and a regio- and stereocontrolled gold(I)-catalyzed N-glycosylation to furnish the purine nucleoside. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3′ in amipurimycin should be of opposite configuration.
Wang, Shengyang,Sun, Jiansong,Zhang, Qingju,Cao, Xin,Zhao, Yachen,Tang, Gongli,Yu, Biao
supporting information
p. 2884 - 2888
(2018/02/16)

Radical cyclization in heterocycle synthesis. Part 13: Sulfanyl radical addition-cyclization of oxime ethers and hydrazones connected with alkenes for synthesis of cyclic β-amino acids
A combination of sulfanyl radical addition-cyclization of the oxime ethers and hydrazones connected with alkenes and subsequent conversion of a phenylsulfanylmethyl group to a carboxyl group provides a novel method for the construction of the cyclic β-amino acids. Upon treatment with thiophenol in the presence of AIBN, the oxime ethers and hydrazones smoothly underwent sulfanyl radical addition-cyclization to give the 2-(phenylsulfanylmethyl)cycloalkylamine. This method was successfully applied to the practical synthesis of 2-aminocyclopentanecarboxylic acid and 4-amino-3-pyrrolidinecarboxylic acid.
Miyata, Okiko,Muroya, Kanami,Kobayashi, Tomoko,Yamanaka, Rina,Kajisa, Seiko,Koide, Junko,Naito, Takeaki
p. 4459 - 4479
(2007/10/03)

A concise synthesis of rigidified β-amino acids via sulfanyl radical addition-cyclization of oxime ethers and hydrazones
A new route to the rigidified cyclic β-amino acids such as cispentacin has been developed by sulfanyl radical addition-cyclization of the alkenyl-tethered-oxime ethers and hydrazones.
Miyata, Okiko,Muroya, Kanami,Koide, Junko,Naito, Takeaki
p. 271 - 272
(2007/10/03)

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
Konosu,Oida
p. 1012 - 1018
(2007/10/02)

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Chemical Properties

Melting Point: 90-94 °C
Boiling Point: 382.5 °C at 760 mmHg
Flash Point:185.1 °C
Density: 1.15 g/cm³
Storage Temp.:2-8°C
Vapor Pressure: 6.55E-07mmHg at 25°C
Refractive Index: 1.495
PKA: 4.53±0.40(Predicted)
PSA: 75.63000
LogP: 2.15530

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