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 1172157Notes

Reaction equation

HRID 1172157 reaction equation
[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.[CH3:26][C@@H:27]([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:28][C:29](=[O:37])[CH2:30]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:30]/[C:29](=[O:37])[CH2:28][C@@H:27]([CH3:26])[CH2:38][CH2:39][CH2:40][CH3:41])[C@H:4]([O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH2:3]1

Participants

3

Reactant 2

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 ester

Product 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

Procedure

By the same procedure as the reaction of Example 6 using methyl (5Z)-7-[(1R,2R,3R,5R)-5-chloro-2-formyl-3-(tetrahydro-2H-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.

Sources & evidence

ORD record
ord-9886857c472d4cd49b1b80cfc75e760e
Source dataset
uspto-grants-2010_11
Patent number
US07833995B2

Reaction notes

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