methyl (5Z)-7-[(1R,2R,3R,5R)-5-chloro-2-formyl-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]-5-heptenoate → Methyl (5Z)-7-{(1R,2R,3R,5R)-5-chloro-2-[(1E,5S)-5-methyl-3-oxo-1-nonenyl]-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl}-5-heptenoate

HRID 1888316

Reaktionsgleichung

Reaktionsgleichung von HRID 1888316
[Cl:1][C@H:2]1[C@H:6]([CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[C@@H:5]([CH:17]=O)[C@H:4]([O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH2:3]1.C([C@H]1COC(=O)N1CCSC1SC=C(C(OCC)=O)N=1)=O.[CH3:47][C@@H:48]([CH2:59][CH2:60][CH2:61][CH3:62])[CH2:49][C:50](=[O:58])[CH2:51]P(=O)(OC)OC>>[Cl:1][C@H:2]1[C@H:6]([CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[C@@H:5](/[CH:17]=[CH:51]/[C:50](=[O:58])[CH2:49][C@@H:48]([CH3:47])[CH2:59][CH2:60][CH2:61][CH3:62])[C@H:4]([O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH2:3]1

Komponenten

4

Edukt 3

HCID 11234130methyl (5Z)-7-[(1R,2R,3R,5R)-5-chloro-2-formyl-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]-5-heptenoateHCID 13018122[(4S)-4-Methyl-2-oxooctyl]phosphonic acid dimethyl esterHCID 86650055HCID 86650055, Verbindung

Produkt 1

HCID 66858265Methyl (5Z)-7-{(1R,2R,3R,5R)-5-chloro-2-[(1E,5S)-5-methyl-3-oxo-1-nonenyl]-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl}-5-heptenoate

Versuchsvorschrift

By the same procedure as the reaction of Example 6 using methyl (5Z)-7-[(1R,2R,3R,5R)-5-chloro-2-formyl-3-(tetrahydro-2 H-pyran-2-yloxy)cyclopentyl]-5-heptenoate (Reg. No. 261772-21-8) instead of the compound 5 and using dimethyl [(4S)-4-methyl-2-oxooctyl]phosphonate instead of dimethyl (3,3-dimethyl-2-oxoheptyl)phosphonate, the title compound (360 mg) having the following physical data was obtained.

Quellen und Nachweise

ORD-Eintrag
ord-e2c8cbb828c54e93a6673f86c31e567f
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501793B2

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