Conversion of p-methoxyphenyl glycosides into the corresponding glycosyl chlorides and bromides, and into thiophenyl glycosides.
p-Methoxyphenyl (pMP) beta-D-glycopyranosides (Glc, Gal, GlcNPhth, GalNPhth, GlcNTroc, Gal beta 4Glc, Gal alpha 4Gal) were prepared from the corresponding 1-O-acetyl sugars in 79-90% yield, using boron trifluoride etherate as promoter. Treatment of the pMP glycosides with acyl chlorides or bromides in the presence of various Lewis acids gave the corresponding glycosyl chlorides and bromides in 81-98% yield. Treatment of the acyl-protected pMP glycosides with thiophenol and boron trifluoride etherate gave the corresponding thioglycosides in 80-100% yield and high (> 20:1) beta/alpha selectivity. The stability of pMP glycosides was investigated against a series of reagents.
Zhang
Z
Z
Organic Chemistry 2, Lund University, Sweden.
Magnusson
G
G
D000840:Anisoles / Q000138:chemical synthesis / Q000378:metabolism; D001880:Boranes / Q000378:metabolism; D005960:Glucosides / Q000138:chemical synthesis; D006027:Glycosides / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D013865:Thioglycosides / Q000138:chemical synthesis*
D000840:Anisoles; D001880:Boranes; D005960:Glucosides; D006027:Glycosides; D013865:Thioglycosides; C101707:boron trifluoride etherate; C031919:4-methoxyphenylglucoside