Sodium hydride → (2S,3S,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 1508440Notes

Reaction equation

HRID 1508440 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]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(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: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:39])[CH:41]=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 18370708Ethyl 3-(3-fluorophenyl)-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 66980235(2S,3S,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 19%

Procedure

The title compound was prepared as described for C4 using ethyl 3-(3-fluorophenyl)-2-oxopropanoate B5 (100 mg, 0.476 mmol), sodium hydride (13 mg, 0.523 mmol) and 2,3,4,6-tetra-O-acetyl-α-D-glucose bromide (196 mg, 0.476 mmol). The compound was isolated in the form of white solid in 19% yield.

Workup

  1. customThe compound was isolated in the form of white solid in 19% yield

Sources & evidence

ORD record
ord-24c152b64fd4461cb3b9289009b4c849
Source dataset
uspto-grants-2015_12
Patent number
US09221860B2

Reaction notes

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