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【结 构 式】

【分子编号】62552

【品名】methyl (3S,4R,5S)-4-{[(2S,3R)-2-amino-3-(benzyloxy)butanoyl]amino}-3-hydroxy-5-methylheptanoate

【CA登记号】

【 分 子 式 】C20H32N2O5

【 分 子 量 】380.48456

【元素组成】C 63.14% H 8.48% N 7.36% O 21.03%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XLIV)

For the synthesis of the other peptidic moiety (L), removal of the N-Boc group from the isostatine derivative (XLI) by means of trifluoroacetic acid gave amino ester (XLII), which was coupled with N-Boc-L-threonine benzyl ether (III) to afford dipeptide (XLIII). Boc group removal in (XLIII) with HCl provided peptide (XLIV), which was coupled with N-Boc-N-methyl-D-leucine (XXVII) to yield tripeptide (XLV). Saponification of the methyl ester group of (XLV) with NaOH provided acid (XLVI). Sequential protection of the alcohol hydroxyl of (XLVI) as the tert-butyldimethylsilyl ether, and esterification of the carboxyl group with trichloroethanol led to the fully protected tripeptide (XLVII). The benzyl ether group of (XLVII) was then removed by catalytic hydrogenolysis to furnish alcohol (XLVIII)

1 Jou, G.; Gonzalez, I.; Albericio, F.; Lloyd-Williams, P.; Giralt, E.; Total synthesis of dehydrodidemnin B. Use of uronium and phosphonium salt coupling reagents in peptide synthesis in solution. J Org Chem 1997, 62, 2, 354.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(III) 50782 (2S,3R)-3-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]butyric acid C16H23NO5 详情 详情
(XXVII) 50788 (2R)-2-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentanoic acid C12H23NO4 详情 详情
(XLI) 62534 methyl (3S,4R,5S)-4-[(tert-butoxycarbonyl)amino]-3-hydroxy-5-methylheptanoate C14H27NO5 详情 详情
(XLII) 62550 methyl (3S,4R,5S)-4-amino-3-hydroxy-5-methylheptanoate C9H19NO3 详情 详情
(XLIII) 62551 methyl (3S,4R,5S)-4-({(2S,3R)-3-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]butanoyl}amino)-3-hydroxy-5-methylheptanoate C25H40N2O7 详情 详情
(XLIV) 62552 methyl (3S,4R,5S)-4-{[(2S,3R)-2-amino-3-(benzyloxy)butanoyl]amino}-3-hydroxy-5-methylheptanoate C20H32N2O5 详情 详情
(XLV) 62553 methyl (6R,9S,12R,13S)-9-[(1R)-1-(benzyloxy)ethyl]-13-hydroxy-6-isobutyl-2,2,5-trimethyl-12-[(1S)-1-methylpropyl]-4,7,10-trioxo-3-oxa-5,8,11-triazapentadecan-15-oate C32H53N3O8 详情 详情
(XLVI) 62554 (6R,9S,12R,13S)-9-[(1R)-1-(benzyloxy)ethyl]-13-hydroxy-6-isobutyl-2,2,5-trimethyl-12-[(1S)-1-methylpropyl]-4,7,10-trioxo-3-oxa-5,8,11-triazapentadecan-15-oic acid C31H51N3O8 详情 详情
(XLVII) 50787 2,2,2-trichloroethyl (6R,9S,12R,13S)-9-[(1R)-1-(benzyloxy)ethyl]-13-[[tert-butyl(dimethyl)silyl]oxy]-6-isobutyl-2,2,5-trimethyl-12-[(1S)-1-methylpropyl]-4,7,10-trioxo-3-oxa-5,8,11-triazapentadecan-15-oate C39H66Cl3N3O8Si 详情 详情
(XLVIII) 50784 2,2,2-trichloroethyl (6R,9S,12R,13S)-13-[[tert-butyl(dimethyl)silyl]oxy]-9-[(1R)-1-hydroxyethyl]-6-isobutyl-2,2,5-trimethyl-12-[(1S)-1-methylpropyl]-4,7,10-trioxo-3-oxa-5,8,11-triazapentadecan-15-oate C32H60Cl3N3O8Si 详情 详情
Extended Information