Potassium Carbonate → HCID 23077013, compound

HRID 1297537Notes

Reaction equation

[C:1](O[C@@H]1[C@@H](OC(=O)C)[C@H](OC(=O)C)[C@@H](COC(=O)C)S[C@H]1Br)(=[O:3])[CH3:2].[CH2:25]([C:27]1[CH:40]=[CH:39][C:30]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[OH:38])=[CH:29][CH:28]=1)[CH3:26].C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.C(Cl)(Cl)Cl>[C:1]([O:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[CH2:31][C:30]1[CH:39]=[CH:40][C:27]([CH2:25][CH3:26])=[CH:28][CH:29]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

2,3,4,6-Tetra-O-acetyl-5-thio-β-D-glucopyranosyl bromide (1) (Tetrahedron, vol. 49, p. 8977, 1993), 2-(4-ethylbenzyl)phenol (9), potassium carbonate and benzyl tri-n-butylammonium chloride were mixed in chloroform and heated at 60° C. However, it was completely impossible to obtain a glycosylation product. 2-(4-Ethylbenzyl)phenyl acetate was obtained as a by-product.

Workup

customto obtain a glycosylation product

Sources & evidence

ORD record: ord-669e082926dc4531afa2c407c67f397e
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250522B2

Reaction notes

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