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【结 构 式】 
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【分子编号】21343 【品名】(2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12,15-tetrahydroxy-6,20-bis[(1R)-1-hydroxyethyl]-16-methyl-9-[[(9E,12E)-9,12-octadecadienoyloxy]amino]hexadecahydro-1H-dipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosine-5,8,14,19,22,25(9H,25aH)-hexone 【CA登记号】 |
【 分 子 式 】C52H81N7O17 【 分 子 量 】1076.25212 【元素组成】C 58.03% H 7.59% N 9.11% O 25.27% |
合成路线1
该中间体在本合成路线中的序号：(I)Cilofungin is a semi-synthetic anti-Candida agent that is derived from a three-step process: a) fermentation, isolation and purification of echinocandin B (ECB) (I) using an Aspergillus nidulans strain as the producing culture; b) deacylation of ECB by fermentation using an Actinoplanes utahensis culture to give the ECB nucleus (II); and c) N-acylation of the amino terminus of (II) using an activated ester of 4-octyloxybenzoic acid to give cilofungin.
| 【1】 Molloy, R.M.; Hunt, A.H.; Debono, M.; Fukuda, D.S, Barnhart, M.; Butler, T.F.; Abbott, B.J.; Willard, K.E.; Turner, J.R.; Michel, K.H.; Synthesis of new analogs of echinocandin B by enzymatic deacylation and chemical reacylation of the echinocandin peptide: Synthesis of the antifungal agent cilofungin (LY-121019). J Antibiot 1989, 42, 389. |
| 【2】 Gordee, R.; Debono, M.; CILOFUNGIN < Prop INN; USAN >. Drugs Fut 1989, 14, 10, 939. |
| 【3】 Knusel, F.; Trechler, H.; Voser, W.; Nefeler, R.; Benz, F.; Keller-Schierlein, W.; Nuesch, J.; Echinocandin B. Ein Neuartiges Polypeptide-antibioticum aus Aspergillus nidulans var echinulatus: Isoleirung and Bausteine. Helv Chim Acta 1974, 57, 2459. |
| 【4】 Abbott, B.J.; Gordee, R.S.; Hunt, A.H.; Zeckner, D.J.; Howard, L.C.; Butler, T.F.; Molloy, R.M.; Debono, M.; Barnhart, M.; Turner, J.R.; Willard, K.E.; Fukuda, D.S.; Synthesis and evaluation of LY-121019, a member of a series of semisynthetic analogues of the antifungal lipopeptide echinocandin B. Ann NY Acad Sci 1988, 152. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 21343 | (2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12,15-tetrahydroxy-6,20-bis[(1R)-1-hydroxyethyl]-16-methyl-9-[[(9E,12E)-9,12-octadecadienoyloxy]amino]hexadecahydro-1H-dipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosine-5,8,14,19,22,25(9H,25aH)-hexone | C52H81N7O17 | 详情 | 详情 | |
| (II) | 16118 | (2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-9-amino-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12,15-tetrahydroxy-6,20-bis[(1R)-1-hydroxyethyl]-16-methylhexadecahydro-1H-dipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosine-5,8,14,19,22,25(9H,25aH)-hexone | C34H51N7O15 | 详情 | 详情 |