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

HRID 1508435Notes

Reaction equation

HRID 1508435 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:19]/[C:20](/[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:21]\[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2F)[O:7][C@H:6]1[CH2:34][O:35][C:36](=[O:38])[CH3:37])(=[O:3])[CH3:2].[Cl:39]C1C=CC(CC(=O)C(OCC)=O)=CC=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:19]/[C:20](/[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:21]\[C:22]2[CH:27]=[CH:26][C:25]([Cl:39])=[CH:24][CH:23]=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 2736395Ethyl 3-(4-chlorophenyl)-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 867023622,3,4,6 tetra-O-acetyl-alpha-D-glucose bromide

Product 1

HCID 66980241(2S,3S,4R,5S,6R)-2-(Acetoxymethyl)-6-(((Z)-1-(4-chlorophenyl)-3-ethoxy-3-oxoprop-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-(4-chlorophenyl)-2-oxopropanoate B7 (100 mg, 0.441 mmol), sodium hydride (11.65 mg, 0.485 mmol) and 2,3,4,6 tetra-O-acetyl-α-D-glucose bromide (181 mg, 0.441 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-57a5dd9f1279489db314c35489957276
Source dataset
uspto-grants-2015_12
Patent number
US09221860B2

Reaction notes

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