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

HRID 1508432Notes

Reaction equation

HRID 1508432 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](O/C(/C(OCC)=O)=C\C2C=CC=CC=2F)[O:7][C@H:6]1[CH2:34][O:35][C:36](=[O:38])[CH3:37])(=[O:3])[CH3:2].[F:39][C:40]([F:56])([F:55])[C:41]1[CH:42]=[C:43]([CH2:47][C:48](=[O:54])[C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH:44]=[CH:45][CH:46]=1.[H-].[Na+].[Br-].C(O[C@@H]1[C@@H](OC(=O)C)[C@@H](OC(=O)C)[C@@H](COC(=O)C)O[C@@H]1O)(=O)C>>[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]([O:54]/[C:48](/[C:49]([O:51][CH2:52][CH3:53])=[O:50])=[CH:47]\[C:43]2[CH:44]=[CH:45][CH:46]=[C:41]([C:40]([F:55])([F:56])[F:39])[CH:42]=2)[O:7][C@H:6]1[CH2:34][O:35][C:36](=[O:38])[CH3:37])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 18370921Ethyl (3-trifluoromethylphenyl)pyruvateHCID 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 66980348(2S,3R,4R,5S,6R)-2-(Acetoxymethyl)-6-(((Z)-3-ethoxy-3-oxo-1-(3 (trifluoromethyl)phenyl)prop-1-en-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetateYield 22%

Procedure

The title compound was prepared as described for C4 using ethyl 3-(3-(trifluoromethyl)phenyl)-2-oxopropanoate B10 (100 mg, 0.384 mmol), sodium hydride (10.14 mg, 0.544 mmol) and 2,3,4,6 tetra-O-acetyl-α-D-galactose bromide (158 mg, 0.384 mmol). The resulting compound was isolated in the form of white solid in 22% yield.

Workup

  1. customThe resulting compound was isolated in the form of white solid in 22% yield

Sources & evidence

ORD record
ord-b5f374cec6464782984fa1ea849543a1
Source dataset
uspto-grants-2015_12
Patent number
US09221860B2

Reaction notes

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