Sodium hydride → (2S,3R,4R,5S,6R)-2-(Acetoxymethyl)-6-(((Z)-3-ethoxy-1-(3-fluorophenyl)-3-oxoprop-1-en-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

HRID 1508451Notes

Reaction equation

HRID 1508451 reaction equation
C(O[C@@H]1[C@@H](OC(=O)C)[C@H](OC(=O)C)[C@@H](O/C(/C(OCC)=O)=C\C2C=CC=CC=2[F:28])O[C@H]1COC(=O)C)(=O)C.Br[C:40]1[CH:41]=[C:42]([CH2:46][C:47](=[O:53])[C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH:43]=[CH:44][CH:45]=1.[H-].[Na+].[Br-].[C:57]([O:60][C@@H:61]1[C@@H:67]([O:68][C:69](=[O:71])[CH3:70])[C@@H:66]([O:72][C:73](=[O:75])[CH3:74])[C@@H:65]([CH2:76][O:77][C:78](=[O:80])[CH3:79])[O:64][C@@H:62]1O)(=[O:59])[CH3:58]>>[C:73]([O:72][C@H:66]1[C@@H:67]([O:68][C:69](=[O:71])[CH3:70])[C@H:61]([O:60][C:57](=[O:59])[CH3:58])[C@@H:62]([O:53]/[C:47](/[C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:46]\[C:42]2[CH:43]=[CH:44][CH:45]=[C:40]([F:28])[CH:41]=2)[O:64][C@H:65]1[CH2:76][O:77][C:78](=[O:80])[CH3:79])(=[O:75])[CH3:74]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 18371018Ethyl 3-(3-bromophenyl)-2-oxopropanoateHCID 66980300(2S,3S,4R,5S,6R)-2-(Acetoxymethyl)-6-(((Z)-3-ethoxy-1-(2-fluorophenyl)-3-oxoprop-1-en-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetateHCID 867023632,3,4,6 tetra-O-acetyl-alpha-D-galactose bromide

Product 1

HCID 66980239(2S,3R,4R,5S,6R)-2-(Acetoxymethyl)-6-(((Z)-3-ethoxy-1-(3-fluorophenyl)-3-oxoprop-1-en-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetateYield 24%

Procedure

The title compound was prepared as described for C4 using Ethyl 3-(3-bromophenyl)-2-oxopropanoate B17 (100 mg, 0.369 mmol), sodium hydride (9.74 mg, 0.406 mmol) and 2,3,4,6-tetra-O-acetyl-α-D-galactose bromide (152 mg, 0.369 mmol). The resulting compound was isolated in the form of white solid in 24% yield.

Workup

  1. customThe resulting compound was isolated in the form of white solid in 24% yield

Sources & evidence

ORD record
ord-fd81e77f97c04f8fae86b454ab8415ee
Source dataset
uspto-grants-2015_12
Patent number
US09221860B2

Reaction notes

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