Boron trifluoride etherate → (3R,4R,5S,6R)-2-(4-Chloro-3-(4-ethoxybenzyl)-5-methoxyphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

HRID 576341Notes

Reaction equation

[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2(OC)[C@H:15]([OH:16])[C@@H:14]([OH:17])[C@H:13]([OH:18])[C@@H:12]([CH2:19][OH:20])[O:11]2)=[CH:4][C:3]=1[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH3:32])=[CH:26][CH:25]=1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC.C([O-])(O)=O.[Na+]>C(Cl)Cl.CC#N>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([CH:10]2[C@H:15]([OH:16])[C@@H:14]([OH:17])[C@H:13]([OH:18])[C@@H:12]([CH2:19][OH:20])[O:11]2)=[CH:4][C:3]=1[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH3:32])=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of triol 74-3 (6.6 g, 14.14 mmol) in CH2Cl2/CH3CN (70 mL/70 mL) were added triethylsilane (4.5 mL, 28.28 mmol) and boron trifluoride diethyl etherate (3.6 mL, 28.28 mmol) at −50° C. The mixture was warmed up to 0° C. slowly and stirred at 0° C. for 2 hours. To the mixture was added aq. saturated NaHCO3 solution (50 mL) slowly and extracted with EtOAc (100 mL×2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was carried on to the next step without purification.

Workup

extractionextracted with EtOAc (100 mL×2)
dry with materialThe combined organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was carried on to the next step without purification

Sources & evidence

ORD record: ord-15811e9171bf4dd2896c5af64fa4484c
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034921B2

Reaction notes

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