2-O-propargyl ethers: readily cleavable, minimally intrusive protecting groups for beta-mannosyl donors.
[reaction: see text]. The use of 2-O-propargyl ethers as protecting groups in 4,6-O-benzylidene-protected mannopyranosyl donors bearing either bulky silyl groups or glycosidic linkages on O3 overcomes the poor stereoselectivity achieved with the corresponding 2-O-benzyl ethers, due to a reduction of steric buttressing. Deprotection is conducted by treatment with potassium tert-butoxide followed by catalytic osmium tetroxide and N-methylmorpholine N-oxide.
Crich
David
D
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dcrich@uic.edu
Jayalath
Prasanna
P
D001597:Benzylidene Compounds / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000737:chemistry*; D007202:Indicators and Reagents; D008362:Mannosides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D001597:Benzylidene Compounds; D004987:Ethers; D007202:Indicators and Reagents; D008362:Mannosides