Highly efficient β-glucosylation of the acidic hydroxyl groups, phenol and carboxylic acid, with an peracetylated glucosyl fluoride using a combination of BF3·Et2O and DTBMP as a promoter

Synlett

Volumn , Issue 10, 1999, Pages 1627-1629

  Oyama, Kin Ichi ^a   Kondo, Tadao ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

1 acylglucose; 2,6 di tertbutyl 4 methylpyridine; BF3 Et2O; Peracetylated glucosyl fluoride; Phenyl glucoside

Indexed keywords

CARBOXYLIC ACID; FLUORIDE; HYDROXYL GROUP; PHENOL DERIVATIVE; PICOLINE DERIVATIVE;

ACETYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GLYCOSYLATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0032826655     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-12529     Document Type: Article

References (21)

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18. 2O / base = 1 / 1.5 / 4 / 4.
19. Using cyclohexanol, a β-phenethyl alcohol, as a glucosyl acceptor, the corresponding glucosyl products were not afforded.
20. 2O / DTBMP = 1 / 1 / 1 / 4 / 4.
21. 4, filtered and concentrated. The residue was purified by silica gel column chromatography (Hexane-AcOEt 1 : 1) to afford phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (41 mg, 98 %).