A new -butyloxycarbonylating reagent, 2--butyloxycarbonyloxyimino-2-phenylacetoni trile.

Itoh, Masumi; Hagiwara, Daijiro; Kitamura, Takashi

doi:10.1016/s0040-4039(00)91133-x

Cited by 166 publications

(60 citation statements)

References 2 publications

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“…Solvents were carefully dried and distilled prior to use or stored under an inert atmosphere, unless denoted otherwise. [ PdCi2(COD) ], [ Pd(Me)CI(COD) ] (COD = cyclo-l,5-octadiene) [9], 2-diphenylphosphine-benzaldehyde [10], [PdCI(B3-CH2C -(Me)CH2) ]2 and [PdCl(r/3-CH2C(Me)C(Me)2) ]2 [5], 31-aminopropyl-ethylsulfide (H2N-Prop-S-Et) Ill] 2 and Ntert-butyloxycarbonyI-L-methionine (BOC-Met-OH) [ 12] were synthesized by literature procedures. Methioninol, 2-tert-butyloxycarbonyloximino-2-phenylacetonitrile (BOC-ON), methionine and 2-pyridine carboxaldehyde are commercially available and were used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Methyl-, acetyl- and allyl-palladium and -platinum complexes containing novel terdentate PNS and NN'S ligands

Ankersmit

Veldman

Spek

et al. 1996

Inorganica Chimica Acta

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A Methyl-, Acetyl-and Allyl-palladium and -Platinum Complexes Containing Novel Terdentate PNS and NN'S Ligands Ankersmit, H.A.; Veldman, N.; Spek, A.L.; Vrieze, K.; van Koten, G. Published in:Inorganica Chimica Acta DOI:10.1016/S0020-1693(96) Link to publication Citation for published version (APA):Ankersmit, H. A., Veldman, N., Spek, A. L., Vrieze, K., & van Koten, G. (1996). A Methyl-, Acetyl-and Allylpalladium and -Platinum Complexes Containing Novel Terdentate PNS and NN'S Ligands. Inorganica Chimica Acta, 252, 339-354. DOI: 10.1016/S0020-1693(96)05333-9 General rightsIt is not permitted to download or to forward/distribute the text or part of it without the consent of the author(s) and/or copyright holder(s), other than for strictly personal, individual use, unless the work is under an open content license (like Creative Commons). Disclaimer/Complaints regulationsIf you believe that digital publication of certain material infringes any of your rights or (privacy) interests, please let the Library know, stating your reasons. In case of a legitimate complaint, the Library will make the material inaccessible and/or remove it from the website. Please Ask the Library: http://uba.uva.nl/en/contact, or a letter to: Library of the University of Amsterdam, Secretariat, Singel 425, 1012 WP Amsterdam, The Netherlands. You will be contacted as soon as possible. Palladium and platinum compounds of the composition [MX(L) ]X and [M(Me)(L)]X (M =Pd, Pt; X=C1, Br, I, O3SCF3) howe boi~n prepared from the appropriate starting materials and the new ligands (L = N-[2-(diphenylphosphino)benzylidene]-L-methioniool (PNS-I), N-[ 2-(diphenylphosphino) benzylidene l-3-propylethylsuifide (PNS-2),N-{N-[ 2-(diphenylphosphino)benzylidene l-D//-,-methio-nyll-tertbutylamine (PNS-3),N-{N-[2-(pyridine)methylidene]-DIL-methionyl}-tert-butylamine (NN'S)). The single crystal X-ray deterrnination of [PtI(PNS-3)]I (3cz) (triclinic, space group PI (No.2) with a= 10.5298(9), b= 11.5584(8), c= 14.545(2) A, a=T/.368(8), /3=84.453(9), y=79.720(7) °, V= 1696.5(3) A3, Z=2, RI =0.0456, wR'2 =0.1195) showed terdentate coordination of the trifuoctional PNS-3 ligand with a six-memhered PN containing metallacycle and a six-membered NS containing metallacycle which is in a chair conformation. The square planar geometry is completed with an iodide atom, while the second iodide atom is non-coordinating. The methylpalladium and -platinum complexes may occur in solution in various isomeric forms, as an equilibrium has been observed between the ionic [ M (Me) (r/3-PNS) ] X and the neutral [ MX(Me) (,/2-PNS) ]. The ~-PNS bonded complex may occur in two conformations, i.e. with the six-membered NS containing part of the ligand in either the chair or boat form. The methyl-palladium and-platinur ~ complexes reactedslowly with CO to form the con'esponding acetyl complexes, with insertion rates which increased in the order CI < Brl < O3SCF 3-and PNS-I < PNS-2 < PNS-3 < NN'S. Complexes [ Pd (r/3-allyl) (PNS-3) ] X (X = Ci, O3SCF a ) with 2-methylallyl and l,l,2-trimeth...

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Section: Methodsmentioning

confidence: 99%

Methyl-, acetyl- and allyl-palladium and -platinum complexes containing novel terdentate PNS and NN'S ligands

Ankersmit

Veldman

Spek

et al. 1996

Inorganica Chimica Acta

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“…Reaction of 84 with hydrogen in the presence of Pd(OH) 2 in a mixed solvent system of methanol ethyl acetate followed by reaction with Boc ON 22 and triethylamine gave bis Boc protected guanidine 87. Then, bromination of the pyrrole in 87 was carried out with bromine and sodium bicarbonate to give bis Boc cylindradine A (88).…”

Section: C18mentioning

confidence: 99%

Synthetic Studies of Oroidin-derived Pyrrole-imidazole Alkaloids

Iwata¹,

Kamijoh²,

Nagasawa

2015

J. Synth. Org. Chem. Jpn.

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“…This minor modification of the recommended procedure (15) has been found to be generally applicable to the synthesis of BOC-amino acids. ' The BOC-protected cysteinylvaline peptide shown in Scheme 3 was unsuitable for an ACV synthesis because of the difficulties (16) associated with the selective removal of the BOC group from 7 (see Scheme 3) prior to coupling with the aminoadipic acid moiety.…”

Section: H5341 $J2 Tripeptide Precursor 6-(l-a-aminoadipy1)-l-cystementioning

confidence: 99%

“…oximino-2-phenylacetonitrile (BOC-ON) (15) in the presence of dicyclohexylamine. This minor modification of the recommended procedure (15) has been found to be generally applicable to the synthesis of BOC-amino acids.…”

Section: H5341 $J2 Tripeptide Precursor 6-(l-a-aminoadipy1)-l-cystementioning

confidence: 99%

Total synthesis of δ-(L-α-aminoadipyl)-L-cysteinyl-D-valine (ACV), a biosynthetic precursor of penicillins and cephalosporins

Wolfe¹,

Jokinen²

1979

Can. J. Chem.

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. 57, 1388 (1979.The title compound has been synthesized as its disulfide by a classical route from the fully protected precursor N-BOC-S-trity~-6-(~-a-aminoadipyl)-~-cysteiny-~-vaine bisbenzhydryl ester. Deprotection has been achieved by oxidative removal of the trityl group with iodine, followed by removal of BOC and benzhydryl using trifluoroacetic acid. The final product is obtained in 23% overall yield from D-valine.SAUL WOLFE et MARK GORDON JOKINEN. Can. J. Chem. 57,1388Chem. 57, (1979.On a synthetise le compose mentionnt dans le titre sous forrne de disulfure par une voie classique a partir du precurseur complktement protege qui est I'ester bisbenzhydrylique de la C2-S bonds (3) of penicillin are formed with reten-In this synthesis, the final product and most of the tion of configuration, to proven chemical mech-intermediates have been obtained in crystalline form anisms. The principal reason for the lack of progress and have been characterized fully. on this aspect of the problem is that studies of the Four syntheses of ACV and (or) its stereoisomers fate of ACV and (or) the role of post-ACV inter-have been reported previously in the literature (6-9). mediates require that protoplasts or protoplast Two of these (6, 7) were directed specifically towards lysates (4) derived from P. chrysogenum or C. the LLL isomer; however, the experimental details of acremonium be employed in the biosynthetic experi-Rudinger's synthesis (6) have not yet been presented, ments. The required techniques have only become and spectroscopic and analytical data were not given available in recent years, as a result of the important for the peptide intermediates and the final product work of Abraham and his co-workers (5).of Bauer's synthesis (7). Only the synthesis of Fawcett There are, therefore, two prerequisites for any et al. (9) has been accompanied by full experimental planned investigation of the oxidative stages of details and microanalytical data for the various penicillin biosynthesis. The first is a protoplast or intermediates. In this latter work, three separate protoplast lysate system that will convert ACV deprotecting steps were needed, and the final product efficiently into penicillin; the second is a supply of was obtained in 8.5% yield from the fully protected labelled ACV. We wish to disclose a new total tripeptide. synthesis of ACV (as its disulfide), which makes thisThe syntheses of Adriaens et al. (8) and Fawcett et compound readily available for biosynthetic studies. al. (9) include an alkaline hydrolysis of a protected

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A new -butyloxycarbonylating reagent, 2--butyloxycarbonyloxyimino-2-phenylacetoni trile.

Cited by 166 publications

References 2 publications

Methyl-, acetyl- and allyl-palladium and -platinum complexes containing novel terdentate PNS and NN'S ligands

Methyl-, acetyl- and allyl-palladium and -platinum complexes containing novel terdentate PNS and NN'S ligands

Synthetic Studies of Oroidin-derived Pyrrole-imidazole Alkaloids

Total synthesis of δ-(L-α-aminoadipyl)-L-cysteinyl-D-valine (ACV), a biosynthetic precursor of penicillins and cephalosporins

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