2018
DOI: 10.1134/s1070428018100251
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Synthesis of meta-Carboranyl-(S)-homocysteine Sulfoxide

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Cited by 5 publications
(18 citation statements)
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“…For the selective functionalization of nido-carborane at position B(9), we used an approach based on the demethylation of 9-dimethylsulfonio-nido-carborane (12), by analogy with known methods, 27d,e,28a followed by alkylation. Treatment of compound 12 with sodium in the presence of naphthalene followed by the action of cesium fluoride led to the cesium salt 9-methylthio-nido-carborane (13) in a moderate yield (Scheme 2). Alkylation of thioester 13 with the δ-iodo derivative of protected (S)-norvaline ( 14) smoothly led to (nido-carboran-9-yl)-5-methylthionorvaline derivative 15 as a zwitterion.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
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“…For the selective functionalization of nido-carborane at position B(9), we used an approach based on the demethylation of 9-dimethylsulfonio-nido-carborane (12), by analogy with known methods, 27d,e,28a followed by alkylation. Treatment of compound 12 with sodium in the presence of naphthalene followed by the action of cesium fluoride led to the cesium salt 9-methylthio-nido-carborane (13) in a moderate yield (Scheme 2). Alkylation of thioester 13 with the δ-iodo derivative of protected (S)-norvaline ( 14) smoothly led to (nido-carboran-9-yl)-5-methylthionorvaline derivative 15 as a zwitterion.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
“…s, B10), −37.3 (d, 1B, J = 143.8 Hz, B1). 13 C{ 1 H} NMR (DMSO-d 6 , 126 MHz) (diastereomers I and II): δ 168.0 (C-1, II), 167.8 (C-1, I), 156.7 (q, J = 37.4 Hz, NCO, (I)), 156.5 (q, J = 37.4 Hz, NCO, (II), 115.5 (q, J = 287.9 Hz, CF 3 (I and II)), 53.11 (OMe, II), 53.07 (OMe, I), 49.5 (C-2, II), 48.7 (C-2, I), 44.9 (br s, CH-carborane, I), 44.5 (br s, CH-carborane, II), 42.0 (C-3, II), 41.9 (C-3, I), 23.9 (SMe, II), 22.6 (SMe,I) ,28.63;H,5.61;N,3.71;S,8.49. Found: C,28.64;H,5.34;N,3.79;S,8.25.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
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“…In this regard, the chemistry of dicarbaboranes [C 2 B 10 H 12 ] and their derivatives has been well investigated [16]. The synthesis of o-carboranes containing unnatural ω-mercapto-amino L-o-carboranyl-alanine 2 [18] as well as o-carboranyl derivatives of (S)-Asparagine 3a and (S)-Glutamine 3b [19], phenylalanine 4 [20] and (S)-m-carboranyl-homocysteine sulfoxide 5 [21], have been published. Our current interest was inspired by the recent synthesis [22] of m-carboranyl-cysteine 6 and its biological evaluation as an agent for Boron Neutron Capture Therapy [23,24] (Figure 1).…”
Section: Introductionmentioning
confidence: 99%