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Hydrophobic Vitamin B12. XI. Preparation, Characterization, and Enantioselective Alkylation of Hydrophobic Vitamin B12 Bearing a Binaphthyl Moiety
http://hdl.handle.net/10228/00006478
http://hdl.handle.net/10228/0000647886f8a27c-f99e-4b06-9296-5be8b0e25220
| 名前 / ファイル | ライセンス | アクション |
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BCSJ65_3094.pdf (879.4 kB)
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| Item type | 学術雑誌論文 = Journal Article(1) | |||||||||||||
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| 公開日 | 2017-12-25 | |||||||||||||
| 資源タイプ | ||||||||||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||||||||||
| 資源タイプ | journal article | |||||||||||||
| タイトル | ||||||||||||||
| タイトル | Hydrophobic Vitamin B12. XI. Preparation, Characterization, and Enantioselective Alkylation of Hydrophobic Vitamin B12 Bearing a Binaphthyl Moiety | |||||||||||||
| 言語 | ||||||||||||||
| 言語 | eng | |||||||||||||
| 著者 |
Murakami, Yukito
× Murakami, Yukito× Hisaeda, Yoshio× Kohno, Hiroshi× 横野, 照尚
WEKO
6794
× Nishioka, Takuya |
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| 抄録 | ||||||||||||||
| 内容記述タイプ | Abstract | |||||||||||||
| 内容記述 | Hydrophobic vitamin B12 derivatives bearing a chiral binaphthyl moiety, hexamethyl 71-decarboxy-71-[(R)-2′-methoxy-1,1′-binaphthyl-2-carboxymethyl]cobyrinate perchlorate [B12–BINAP(R)] and hexamethyl 71-decarboxy-71-[(S)-2′-methoxy-1,1′-binaphtyl-2-carboxymethyl]cobyrinate perchlorate [B12–BINAP(S)], were prepared from cyanocobalamin. These complexes were characterized by means of electronic and circular dichroism spectroscopy as well as by cyclic voltammetry in comparison with those data for a hydrophobic vitamin B12 without a binaphthyl moiety. The enantioselective alkylation of hydrophobic vitamin B12 derivatives at the β-axial site was examined in methanol with various 3-bromo-2-methylpropionic esters by means of 1H NMR spectroscopy. All the hydrophobic vitamin B12 derivatives used here, the one bearing methoxycarbonyl groups as peripheral substituents without a binaphthyl moiety, B12–BINAP(R), and B12-BINAP(S), were found to bind (S)-2-methylpropionates more favorably than the corresponding R-enantiomers; the highest S-selectivity was observed with the latter two derivatives, 65% e.e. The cause of such S-enantioselectivity was discussed with attention to stereochemical configurations of the peripheral substituents placed in the corrin ring. | |||||||||||||
| 書誌情報 |
Bulletin of the Chemical Society of Japan 巻 65, 号 11, p. 3094-3102, 発行日 1992-11 |
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| 出版社 | ||||||||||||||
| 出版者 | 公益社団法人日本化学会 | |||||||||||||
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| 関連タイプ | isIdenticalTo | |||||||||||||
| 識別子タイプ | DOI | |||||||||||||
| 関連識別子 | https://doi.org/10.1246/bcsj.65.3094 | |||||||||||||
| NCID | ||||||||||||||
| 収録物識別子タイプ | NCID | |||||||||||||
| 収録物識別子 | AA00580132 | |||||||||||||
| ISSN | ||||||||||||||
| 収録物識別子タイプ | ISSN | |||||||||||||
| 収録物識別子 | 0009-2673 | |||||||||||||
| ISSN | ||||||||||||||
| 収録物識別子タイプ | ISSN | |||||||||||||
| 収録物識別子 | 1348-0634 | |||||||||||||
| 著作権関連情報 | ||||||||||||||
| 権利情報 | Copyright (c) 1992 The Chemical Society of Japan | |||||||||||||
| 出版タイプ | ||||||||||||||
| 出版タイプ | VoR | |||||||||||||
| 出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||||||||||
| 査読の有無 | ||||||||||||||
| 値 | yes | |||||||||||||
| 研究者情報 | ||||||||||||||
| URL | https://hyokadb02.jimu.kyutech.ac.jp/html/98_ja.html | |||||||||||||
| 論文ID（連携） | ||||||||||||||
| 値 | 10025768 | |||||||||||||
| 連携ID | ||||||||||||||
| 値 | 6348 | |||||||||||||
