Sodium hydride → (2R,3S,4R,5S,6S)-2-(((Z)-1-([1,1'-Biphenyl]-3-yl)-3-ethoxy-3-oxoprop-1-en-2-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

HRID 1508447Notes

Reaction equation

HRID 1508447 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].[H-].[Na+].[Br-].C(O[C@@H:46]1[C@@H:52](OC(=O)C)[C@H:51](OC(=O)C)[C@@H:50]([CH2:61]OC(=O)C)O[C@@H:47]1O)(=O)C>>[C:16]([O:15][C@H:9]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:5]([O:4][C:1](=[O:3])[CH3:2])[C@H:6]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[O:7][C@@H:8]1[O:19]/[C:20](/[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:21]\[C:22]1[CH:27]=[C:26]([C:47]2[CH:46]=[CH:52][CH:51]=[CH:50][CH:61]=2)[CH:25]=[CH:24][CH:23]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 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 67117960(2R,3S,4R,5S,6S)-2-(((Z)-1-([1,1'-Biphenyl]-3-yl)-3-ethoxy-3-oxoprop-1-en-2-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetateYield 16%

Procedure

The title compound was prepared as described for C4 using ethyl 3-(3-arylphenyl)-2-oxopropanoate (B14) (100 mg, 0.373 mmol), sodium hydride (9.0 mg, 0.373 mmol) and 2,3,4,6-tetra-O-acetyl-α-D-glucose bromide (153 mg, 0.373 mmol). The compound was isolated in the form of white solid in 16% yield.

Workup

  1. customThe compound was isolated in the form of white solid in 16% yield

Sources & evidence

ORD record
ord-919008cc34cc4bafa1f6b23fa521b175
Source dataset
uspto-grants-2015_12
Patent number
US09221860B2

Reaction notes

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