HCID 67062970, compound → HCID 67063057, compound

HRID 1244193Notes

Reaction equation

HRID 1244193 reaction equation
[C:1]([O:9][C@@H:10]1[CH2:18][C@H:17]([O:19][C:20](=O)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:16]([CH2:28][O:29][C:30](=O)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:15][C@H:11]1[S:12][CH2:13][CH3:14])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)(Cl)Cl>[CH2:1]([O:9][C@@H:10]1[CH2:18][C@H:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@@H:16]([CH2:28][O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[O:15][C@H:11]1[S:12][CH2:13][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 67062970HCID 67062970, compound

Product 1

HCID 67063057HCID 67063057, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Compound 25 (608 mg, 1.17 mmol) gave 364 mg substantially pure product (65%). [α]D=−11.8° (c=1, CHCl3); 1H NMR (CDCl3) 7.44–7.14 (m, 15H), 4.74 (d, 1H, J=11.6 Hz), 4.66–4.56 (m, 4H), 4.50 (d, 1H, J=9.4 Hz), 4.45 (d, 1H, J=11.4 Hz), 3.83 (d, 1H, J=10.7 Hz), 3.69 (dd, 1H, J=4.4, 10.7 Hz), 3.49 (m, 2H), 3.35 (m, 1H), 2.79 (m, 2H), 2.69 (m, H), 1.54 (m, 1H), 1.35 (t, 3H, J=7.3 Hz); 13C NMR (CDCl3): 138.8, 138.4, 135.8, 128.9, 128.7, 128.4, 128.2, 128.1, 127.4, 86.9, 81.3, 75.6, 73.8, 73.3, 72.5, 71.6, 69.8, 45.3, 36.7, 25.1, 20.3, 15.5; MS: calcd for C29H34O4SNa 501.2, found m/z 501.0 (M+Na).

Sources & evidence

ORD record
ord-06a93b55c4774de9b2f93a8bdf511657
Source dataset
uspto-grants-2006_10
Patent number
US07122359B2

Reaction notes

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