تفاعل #705757

ord-44211b30b3a648a8a216dea4235cd91a

معادلة التفاعل

COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
( 1 )
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
Cryptophycin 1
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
( 1 )
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
Cryptophycin 1
COc1ccc(C[C@H](N)C(=O)O)cc1Cl
3-chloro-4-hydroxyphenylalanine
COc1ccc(C[C@H](N)C(=O)O)cc1Cl
3-chloro-4-methoxyphenylalanine
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
( 7 )
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
Cryptophycin
CC(C)CC(O)C(=O)O
leucic acid
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
( 2 )
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
Cryptophycin
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
( 3 )
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
Cryptophycin 3
COc1ccc(C[C@H]2NC(=O)/C=C\C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1
( 4 )
COc1ccc(C[C@H]2NC(=O)/C=C\C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1
Cryptophycin 4
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
( 3 )
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
Cryptophycin 3
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
( 3 )
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
Cryptophycin 3
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
( 7 )
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
Cryptophycin
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
( 2 )
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
Cryptophycin
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
( 1 )
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
Cryptophycin 1
COC(=O)[C@H](C)CNC(=O)[C@@H](Cc1ccc(OC)c(Cl)c1)NC(=O)/C=C/C[C@@H]1O[C@@H](c2ccccc2)[C@H](O)[C@H]1C
( 6 )
COC(=O)[C@H](C)CNC(=O)[C@@H](Cc1ccc(OC)c(Cl)c1)NC(=O)/C=C/C[C@@H]1O[C@@H](c2ccccc2)[C@H](O)[C@H]1C
Cryptophycin 6
COc1ccc(C[C@H]2NC(=O)/C=C\C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1
( 4 )
COc1ccc(C[C@H]2NC(=O)/C=C\C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1
Cryptophycin 4
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
( 2 )
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
Cryptophycin
CC(CN)C(=O)O
3-amino-2-methylpropionic acid
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
( 3 )
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
Cryptophycin 3
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
( 1 )
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
Cryptophycin 1
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
( 2 )
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
Cryptophycin
COC(=O)[C@H](C)CNC(=O)[C@@H](Cc1ccc(OC)c(Cl)c1)NC(=O)/C=C/C[C@@H]1O[C@@H](c2ccccc2)[C@H](O)[C@H]1C
( 6 )
COC(=O)[C@H](C)CNC(=O)[C@@H](Cc1ccc(OC)c(Cl)c1)NC(=O)/C=C/C[C@@H]1O[C@@H](c2ccccc2)[C@H](O)[C@H]1C
Cryptophycin 6
COc1ccc(C[C@H]2NC(=O)/C=C\C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1
( 4 )
COc1ccc(C[C@H]2NC(=O)/C=C\C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1
Cryptophycin 4
CC(C(O)CC=CC(=O)O)C(O)C(O)c1ccccc1
8-epoxy-5-hydroxy-6-methyl-8-phenyl-2-octenoic acid
CC(C(O)CC=CC(=O)O)C(O)C(O)c1ccccc1
5,7,8-trihydroxy-6-methyl-8-phenyl-2-octenoic acid
→
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)CCNC2=O)cc1Cl
Cryptophycin 16

المتفاعلات

—
( 8 )
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
( 1 )
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
Cryptophycin 1
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
( 1 )
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
Cryptophycin 1
—
( 55 )
COc1ccc(C[C@H](N)C(=O)O)cc1Cl
3-chloro-4-hydroxyphenylalanine
COc1ccc(C[C@H](N)C(=O)O)cc1Cl
3-chloro-4-methoxyphenylalanine
—
( 9 )
—
( 5 )
—
( 66/27 )
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
( 7 )
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
Cryptophycin
CC(C)CC(O)C(=O)O
leucic acid
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
( 2 )
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
Cryptophycin
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
( 3 )
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
Cryptophycin 3
COc1ccc(C[C@H]2NC(=O)/C=C\C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1
( 4 )
COc1ccc(C[C@H]2NC(=O)/C=C\C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1
Cryptophycin 4
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
( 3 )
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
Cryptophycin 3
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
( 3 )
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
Cryptophycin 3
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
( 7 )
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
Cryptophycin
—
( 47/16 )
—
( 9 )
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
( 2 )
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
Cryptophycin
—
( ε )
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
( 1 )
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
Cryptophycin 1
COC(=O)[C@H](C)CNC(=O)[C@@H](Cc1ccc(OC)c(Cl)c1)NC(=O)/C=C/C[C@@H]1O[C@@H](c2ccccc2)[C@H](O)[C@H]1C
( 6 )
COC(=O)[C@H](C)CNC(=O)[C@@H](Cc1ccc(OC)c(Cl)c1)NC(=O)/C=C/C[C@@H]1O[C@@H](c2ccccc2)[C@H](O)[C@H]1C
Cryptophycin 6
—
( 12 )
—
( 11/13 )
COc1ccc(C[C@H]2NC(=O)/C=C\C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1
( 4 )
COc1ccc(C[C@H]2NC(=O)/C=C\C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1
Cryptophycin 4
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
( 2 )
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
Cryptophycin
—
( 5 )
—
( 93 )
CC(CN)C(=O)O
3-amino-2-methylpropionic acid
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
( 3 )
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
Cryptophycin 3
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
( 1 )
COc1ccc(C[C@H]2NC(=O)/C=C/C[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
Cryptophycin 1
—
( 10/14 )
—
( 5 )
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
( 2 )
COc1ccc(CC2NC(=O)/C=C/CC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
Cryptophycin
COC(=O)[C@H](C)CNC(=O)[C@@H](Cc1ccc(OC)c(Cl)c1)NC(=O)/C=C/C[C@@H]1O[C@@H](c2ccccc2)[C@H](O)[C@H]1C
( 6 )
COC(=O)[C@H](C)CNC(=O)[C@@H](Cc1ccc(OC)c(Cl)c1)NC(=O)/C=C/C[C@@H]1O[C@@H](c2ccccc2)[C@H](O)[C@H]1C
Cryptophycin 6
COc1ccc(C[C@H]2NC(=O)/C=C\C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1
( 4 )
COc1ccc(C[C@H]2NC(=O)/C=C\C[C@@H]([C@H](C)/C=C/c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1
Cryptophycin 4
—
( 100 )
CC(C(O)CC=CC(=O)O)C(O)C(O)c1ccccc1
8-epoxy-5-hydroxy-6-methyl-8-phenyl-2-octenoic acid
CC(C(O)CC=CC(=O)O)C(O)C(O)c1ccccc1
5,7,8-trihydroxy-6-methyl-8-phenyl-2-octenoic acid
—
( 8 )

الكواشف

لا شيء

المذيبات

CO
MeOH

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

الإجراء التجريبي

[α]D +41.3°(MeOH, c 5.2); UV λmax (ε) 242 (4963), 280 (2430), 286 (2212); IR (neat) νmax 3402, 3270, 2960, 1748, 1724, 1676, 1514, 1466, 1343, 1239, 1177 cm-1 ; EIMS m/z (rel intensity) 640/642 (66/27), 398/400 (47/16), 265 (55), 227 (93), 181 (100); high resolution EIMS m/z 640.25676 (calcd for C34H41ClN2O8b , -1.6 mmu error). 1H NMR (CDCl3): amino or hydroxyacid unit δ (carbon position, multiplicity; J in Hz) 7, 8-epoxy-5-hydroxy-6-methyl-8-phenyl-2-octenoic acid (A) 5.74 (2, d; 16), 6.67 (3, ddd; 15.3, 9.7 and 5.5), 2.45 (4, dt; 14.3 and 10.4), 2.55 (4, brdd; 14.3 and 5.3), 5.15 (5, ddd; 11.2, 4.8 and 1.8), 1.8 (6, m), 1.14 (6-Me, d; 7.0), 2.92 (7, dd; 7.5 and 2.0), 3.69 (8, d; 2.0), 7.24-7.26 (10/14, m), 7.33-7.39 (11/12/13, m); 3-chloro-4-hydroxyphenylalanine (B) 4.8 (2, m), 5.64 (2-NH, d; 8.8), 3.03 (3, dd; 14.5 and 7.0), 3.11 (3, dd; 14.4 and 5.6), 7.17 (5, d; 2.2), 5.61(7-OH, s), 6.91 (8, d; 8.3), 7.0 (9, dd; 8.3 and 2.2); 3-amino-2-methylpropionic acid (C) 2.71 (2, m), 1.22 (2-Me, d; 7.3), 3.28 (3, dt; 13.6 and 6.8), 3.49 (3, ddd; 13.6, 5 and 4.1), 6.92 (3-NH, br t; 6.1); leucic acid (D) 4.83 (2, dd; 10.1 and 3.3), 1.36 (3, m), 1.67-1.75 (3, m), 1;67-1.75 (4, m), 0.85 (5, d; 7.5), 0.86 (5', d; 6.8). 13C NMR (CDCl3) unit δ (carbon position) A 165.3 (1), 125.3 (2), 141.0 (3), 36.7 (4), 76.2 (5), 40.6 (6), 13.5 (6-Me), 63.0 (7), 59.0 (8), 136.8 (9), 125.6 (10/14), 128.7 (11/13), 128.6 (12); B 170.9 (1), 53.6 (2), 35.1 (3), 129.9 (4), 129.6 (5), 120.0 (6), 150.4 (7), 116.4 (8), 129.2 (9); C 175.6 (1), 38.3 (2), 14.1 (2-Me), 41.1 (3); D 170.8 (1), 71.3 (2), 39.4 (3), 24.6 (4), 21.3 (5), 22.9 (5').

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05952298uspto-grants-1999_09