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

HRID 1508443Notes

Reaction equation

HRID 1508443 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].[CH3:39]C1C=C(CC(=O)C(OCC)=O)C=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]=[C:26]([CH3:39])[CH:25]=[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 18370163Ethyl (3-methylphenyl)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 867023622,3,4,6 tetra-O-acetyl-alpha-D-glucose bromide

Product 1

HCID 66980200(2S,3S,4R,5S,6R)-2-(Acetoxymethyl)-6-(((Z)-3-ethoxy-3-oxo-1-(m-tolyl)prop-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-methylphenyl)-2-oxopropanoate B18 (100 mg, 0.485 mmol), sodium hydride (11.64 mg, 0.485 mmol) and 2,3,4,6-tetra-O-acetyl-α-D-glucose bromide (199 mg, 0.485 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-40870085cafd4cc8a5920aa2511e50b6
Source dataset
uspto-grants-2015_12
Patent number
US09221860B2

Reaction notes

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