4-Hydroxybenzaldehyde → HCID 15840208, compound

HRID 1820606Notes

Reaction equation

[CH3:1][O:2][C:3]([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](=[O:22])[CH3:21])[C@H:7](Br)[O:6]1)=[O:4].[OH:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][CH:26]=1>>[CH3:1][O:2][C:3]([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](=[O:22])[CH3:21])[C@H:7]([O:24][C:25]2[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][CH:26]=2)[O:6]1)=[O:4]

Participants

Reactant 2

HCID 1264-Hydroxybenzaldehyde

HCID 10916287HCID 10916287, compound

Product 1

HCID 15840208HCID 15840208, compoundYield 72.1%

Procedure

44.1 g (111 mmol) of (2S,3S,4S,5R,6S)-3,4,5-triacetoxy-6-bromo-tetrahydro-pyran-2-carboxylic acid methyl ester is reacted analogously to Example LE1a with 14 g of 4-hydroxy-benzaldehyde, and after working-up and purification, 35.1 g (80 mmol, 72%) of the title compound is isolated.

Workup

custompurification

Sources & evidence

ORD record: ord-bbeb0a874e954c958afe46af450e9dc0
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605136B2

Reaction notes

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