Potassium Phosphate, Tribasic → (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(5-(4-ethylbenzyl)-3,4-dimethylthiophen-2-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

HRID 1469205Notes

Reaction equation

[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[S:20][C:21]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][CH3:34])=[CH:29][CH:28]=3)=[C:22]([CH3:25])[C:23]=2Br)[O:7][C@@H:6]1[CH2:35][O:36][C:37](=[O:39])[CH3:38])(=[O:3])[CH3:2].[CH3:40]B1OB(C)OB(C)O1.F[B-](F)(F)F.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[S:20][C:21]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][CH3:34])=[CH:29][CH:28]=3)=[C:22]([CH3:25])[C:23]=2[CH3:40])[O:7][C@@H:6]1[CH2:35][O:36][C:37](=[O:39])[CH3:38])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(3-bromo-5-(4-ethylbenzyl)-4-methylthiophen-2-yl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate (56) (200 mg, 0.320 mmole) in toluene/water (4 mL/2 mL) were added trimethylboroxine (134 μL, 0.960 mmole), Pd(OAc)2 (7.2 mg, 0.0320 mmole), tricylcohexylphosphine tetrafluoroborate (23.6 mg, 0.0640 mmole), and K3PO4 (272 mg, 1.28 mmole). The mixture was stirred at 100° C. overnight. The reaction mixture was filtered through celite bed and concentrated in vacuo. The crude residue was purified on Biotage® purification apparatus to yield the title compound 57 (125 mg, 0.223 mmole, 70%) as a yellow solid. [M+Na]+ 583.

Workup

filtrationThe reaction mixture was filtered through celite bed
concentrationconcentrated in vacuo
customThe crude residue was purified on Biotage® purification apparatus

Sources & evidence

ORD record: ord-b04b6d59fee94df1b74a3cec682e0949
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006187B2

Reaction notes

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