Stereoselective synthesis of C-[2-S-(p-tolyl)-2-thio-beta-D-galactopyranosyl] compounds using the reaction of TolSCl adducts of D-galactal with C-nucleophiles.
Pyranosyl chlorides prepared in situ from tri-O-benzyl-D-galactal and TolSCl react with silyl enol ethers, allyltrimethylsilane, and vinyl ethers to give a mixture of beta-C-galacto and alpha-C-talopyranosides in a ratio of 19:1.
Han
M
M
Department of Chemistry, University of North Dakota, Grand Forks 58202-9024, USA.
Smoliakova
I P
IP
Koikov
L N
LN
D002244:Carbon / Q000737:chemistry; D004986:Ether / Q000737:chemistry; D005690:Galactose / Q000031:analogs & derivatives* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism; D013862:Thiogalactosides / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry
D012821:Silanes; D013862:Thiogalactosides; D014753:Vinyl Compounds; D004986:Ether; C002038:galactal; C100195:vinyl ether; D002244:Carbon; D005690:Galactose