تفاعل #705763

ord-762d08c1800349b6a0e013c6b080602b

معادلة التفاعل

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@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=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](N)C(=O)O)cc1Cl
3-chloro-4-methoxyphelylalanine
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
( 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(C)CC(O)C(=O)O
leucic 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
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(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(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(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]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
CC(CN)C(=O)O
3-aminopropionic acid
CC(CN)C(=O)O
3-amino-2-methylpropionic acid
CC(C(O)CC=CC(=O)O)C(O)C(O)c1ccccc1
5-hydroxy-6-methyl-8-phenyl-2,7-octadienoic acid
CC(C(O)CC=CC(=O)O)C(O)C(O)c1ccccc1
5,7,8-trihydroxy-6-methyl-8-phenyl-2-octenoic acid
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@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
( 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(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)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)CCNC2=O)cc1Cl
Cryptophycin 29

المتفاعلات

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
—
( 9 )
—
( 9 )
—
( 100 )
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
—
( 5 )
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
—
( 2.6/1.1 )
—
( 95 )
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 )
—
hydroxy acid
COc1ccc(C[C@H](N)C(=O)O)cc1Cl
3-chloro-4-methoxyphelylalanine
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
( 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(C)CC(O)C(=O)O
leucic acid
—
( 8 )
—
( 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)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
—
( 44/15 )
—
( 5 )
—
( 10/14 )
—
( ε )
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(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
—
( 8 )
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(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]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
—
( 50/16 )
CC(CN)C(=O)O
3-aminopropionic acid
CC(CN)C(=O)O
3-amino-2-methylpropionic acid
—
NMR(CDCl3) amino
CC(C(O)CC=CC(=O)O)C(O)C(O)c1ccccc1
5-hydroxy-6-methyl-8-phenyl-2,7-octadienoic acid
CC(C(O)CC=CC(=O)O)C(O)C(O)c1ccccc1
5,7,8-trihydroxy-6-methyl-8-phenyl-2-octenoic acid
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@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
—
( 5 )
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
—
( 12 )
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
—
( 59/20 )
—
( 63 )
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

الكواشف

لا شيء

المذيبات

ClC(Cl)Cl
CHCl3

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

الإجراء التجريبي

[α]D +22.2°(CHCl3, c 1.13); UV λmax (ε) 250 (17000), 284 (3300); IR (neat) νmax 3415, 3272, 2960, 1744, 1734, 1674, 1504, 1259, 1197, 1174, 1067, 694 cm-1 ; EIMS m/z (rel intensity) 624/626 (2.6/1.1), 398/400 (44/15), 227 (100), 195/197 (50/16), 155/157 (59/20), 131 (63), 91 (95); high resolution EIMS m/z 624.2607(calcd for C34H41ClN2O7, -0.5 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) 5.75 (2, dd; 15.3 and 1.1), 6.69 (3, ddd; 15.3, 10.1 and 5.3), 2.36 (4, m), 2.54 (4, m), 5.03 (5, ddd; 11.0, 6.4 and 1.8), 2.56 (6, m), 1.14 (6-Me, d; 6.8), 6.01 (7, dd; 15.8 and 8.8), 6.41 (8, d; 15.8), 7.28-7.33 (10/11/13/14, m), 7.22 (12, m); 3-chloro-4-methoxyphelylalanine (B) 4.76 (2, m), 5.67 (2-NH, d; 8.6), 3.0 (3, dd; 14.4 and 10.2), 3.14 (3, dd; 14.4 and 5.9), 7.22 (5, d; 2.2), 3.87 (7-OMe, s), 6.83 (8, d; 8.4), 7.08 (9, dd; 8.4 and 2.2); 3-aminopropionic acid (C) 2.55 (2-H2, m), 3.44 (3, m), 3.55 (3, m), 6.89 (3-NH, br t; 5.7); leucic acid (D) 4.90 (2, dd; 9.9 and 3.5), 1.34 (3, ddd; 15.4, 10.3 and 3.5), 1.63 (3, m), 1.63 (4, m). 0.76 (4-Me, d; 6.4), 0.72 (5, d; 6.4); 13C NMR (CDCl3) unit δ (carbon position) A 165.6 (1), 125.2 (2), 141.5 (3), 36.4 (4), 77.1 (5), 42.3 (6), 17.3 (6-Me), 130.1 (7), 131.8 (8), 136.7 (9), 126.2 (10/14), 128.6 (11/13), 127.6 (12); B 170.9 (1), 53.8 (2), 34.9 (3), 129.9 (4), 131.0 (5), 122.4 (6), 153.9 (7), 56.1 (7-OMe), 112.2 (8), 128.4 (9); C 172.6 (1), 32.4 (2), 34.5 (3); D 170.4 (1), 71.5 (2), 39.7 (3), 24.4 (4), 21.2 (4-Me), 22.6 (5).

المصدر

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