Beta-Aminoisobutyric Acid → Cryptophycin 50

HRID 618899노트

반응식

HRID 618899 반응식
[OH:1][CH:2]([CH:9]([CH3:20])[CH:10]([OH:19])[CH:11](O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][CH:4]=[CH:5][C:6]([OH:8])=O.Cl[C:22]1[CH:23]=[C:24]([CH:31]=[C:32]([Cl:36])[C:33]=1[O:34][CH3:35])[CH2:25][C@@H:26]([C:28]([OH:30])=O)[NH2:27].[NH2:37][CH2:38][CH:39]([CH3:43])[C:40]([OH:42])=[O:41].[C:44](O)(=[O:51])[CH:45]([CH2:47][CH:48](C)[CH3:49])O>CO>[CH3:49][CH2:48][CH2:47][C@@H:45]1[O:42][C:40](=[O:41])[C@H:39]([CH3:43])[CH2:38][NH:37][C:28](=[O:30])[C@@H:26]([CH2:25][C:24]2[CH:23]=[CH:22][C:33]([O:34][CH3:35])=[C:32]([Cl:36])[CH:31]=2)[NH:27][C:6](=[O:8])[CH:5]=[CH:4][CH2:3][C@@H:2]([C@@H:9]([C@H:10]2[O:19][C@@H:11]2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:20])[O:1][C:44]1=[O:51]

참가 물질

6

반응물 4

HCID 64956Beta-Aminoisobutyric AcidHCID 92779(+-)-2-Hydroxyisocaproic acidHCID 540066555,7,8-Trihydroxy-6-methyl-8-phenyl-2-octenoic acidHCID 545644093,5-Dichloro-4-methoxyphenylalanine

생성물 1

HCID 10722801Cryptophycin 50

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

[α]D +68.1° (MeOH, c 0.075); UV λmax (ε) 246 (25500), 284 (5200); IR (neat) νmax 3401, 3282, 2962, 1744, 1728, 1668, 1540, 1505, 1464, 1258, 1198, 1177, 1066, 694 cm-1 ; EIMS m/z (rel intensity) 624/626 (0.8/0.3), 398/400 (43/14), 227(78), 195/197 (58/26) 91 (100); high resolution EIMS m/z 624.2650 (calcd for C34H41ClN2O7, -4.8 mmu error); 1H-NMR(CDCl3):amino or hydroxy acid unit δ (carbon position, multiplicity; J in Hz) 5-hydroxy-6-methyl-8-phenyl-2,7-octadienoic acid (A) 5.77 (2, d; 14.1), 6.67 (3, m), 2.38 (4, m), 2.50 (4, m), 5.01 (5, m), 2.56 (6, m), 1.13 (6-Me, d; 6.5), 6.03 (7, dd; 15.8 and 8.6), 6.42 (8, d; 15.8), 7.29-7.35 (10/11/13/14, m), 7.23 (12; m); 3-chloro-4-methoxyphenylalanine (B) 4.82 (2, m), 5.64 (2-NH, m), 3.06 (3, m), 3.13 (3, m), 7.22 (5, m), 3.87 (7-OMe, s), 6.83 (8, m), 7.08 (9, m); 3-amino-2-methylpropionic acid (C) 2.72 (2, m), 1.22 (2-Me, d; 6.7), 3.26 (3, m), 3.53 (3, m), 6.90 (3-NH, m); 2-hydroxyvaleric acid (D) 4.81 (2, dd; 8.8 and 3.9), 1.63 (3, m), 1.68 (3, m), 1.33 (4-H2, m). 0.74 (5, t; 7.3).

출처 및 근거

ORD 기록
ord-7f6212d4dd1748559701ca9fca73ab45
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05955423

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