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

HRID 1508453Notes

Reaction equation

HRID 1508453 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]C)=[O:30])=[CH:21]\[C:22]2C=C[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].O=C(CC1[S:47]C=CC=1)C(OC)=O.[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][CH3:32])=[O:30])=[CH:21]\[C:22]2[S:47][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 20277529Methyl 2-oxo-3-(2-thienyl)propionateHCID 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 66980333(2S,3S,4R,5S,6R)-2-(Acetoxymethyl)-6-(((Z)-3-methoxy-3-oxo-1-(thiophen-2-yl)prop-1-en-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetateYield 18%

Procedure

The title compound was prepared as described for C4 using methyl 2-oxo-3-(thiophen-2-yl)propanoate B15 (Otava, 100 mg, 0.543 mmol), sodium hydride (13.03 mg, 0.373 mmol) and 2,3,4,6-tetra-O-acetyl-α-D-glucose bromide (223 mg, 0.543 mmol). The compound was isolated in the form of white solid in 18% yield.

Workup

  1. customThe compound was isolated in the form of white solid in 18% yield

Sources & evidence

ORD record
ord-cfe4c7ee0e244af599cad4a3aa09284c
Source dataset
uspto-grants-2015_12
Patent number
US09221860B2

Reaction notes

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