000059626 001__ 59626
000059626 005__ 20180317092301.0
000059626 022__ $$a0957-4166
000059626 037__ $$aARTICLE
000059626 245__ $$aNaked Sugars as Synthetic Intermediates .26. Synthesis of Alpha-D-(1-]3) and Alpha-D-(1-]4)-C-Linked Galactosides of D-Mannose Derivatives - Conformation of Alpha-C-Galactosides
000059626 260__ $$c1994
000059626 269__ $$a1994
000059626 336__ $$aJournal Articles
000059626 500__ $$aUniv lausanne,bch dorigny,chim sect,ch-1015 lausanne,switzerland.
000059626 520__ $$aReductive radical alpha-D-galactosidation of 5-exo-(benzeneselenyl)-6-endo-chloro-3-methylidene-7- -oxabicyclo[2.2.1]heptan-2-one with acetobromo-D-galactose, followed by ketone reduction led to (+)-(1R,2S, 3R,4S,5S,6S)-5-exo-(benzeneselenyl)-6-endo-chloro-3-endo-[(2',3',4',6'-t etra-O-acetyl-alpha-D-galactopyranosyl)me- thyl]-7-oxabicyclo[2.2.1]heptan-2-endo-ol which was converted into (+)-methyl 3-deoxy-3-[(alpha-D-galactopyranosyl)methyl]-alpha-D-mannopyranoside (1), (+)-3-deoxy-3-[alpha-D-galactopyranosyl)methyl]-D-mannitol (2) and 4-deoxy-4-[(2',3',4',6'-tetra-O-acetyl-alpha-D-galactopyranosyl)methyl]- 2,3,6-tri-O-acetyl-D-mannono-1,5-lactone (3). H-1-MNR data of the alpha-C-galactosides confirmed that their preferred conformations involve antiperiplanar arrangements for the C-linked substrates and bond sigma C(1'),C(2') of the alpha-(1-->3)-C-galactoside unit. The alpha-(1-->3)-C-galactoside of methyl mannopyranoside 1 adopts a conformation similar to that proposed for methyl 3-O-(alpha-D-galactopyranosyl)-alpha-D-mannopyranoside.
000059626 6531_ $$aD-glycopyranosyl phenylsulfones
000059626 6531_ $$apreferred conformation
000059626 6531_ $$asyncytium
000059626 6531_ $$aformation
000059626 6531_ $$avinyl carbanions
000059626 6531_ $$abond formation
000059626 6531_ $$adisaccharides
000059626 6531_ $$aglycosides
000059626 6531_ $$ainhibitors
000059626 6531_ $$achemistry
000059626 6531_ $$aadditions
000059626 700__ $$aFerritto, R.
000059626 700__ $$0240222$$aVogel, P.$$g123681
000059626 773__ $$j5$$k11$$q2077-2092$$tTetrahedron-Asymmetry
000059626 909CO $$ooai:infoscience.tind.io:59626$$particle$$pSB
000059626 909C0 $$0252076$$pLGSA$$xU10111
000059626 937__ $$aLGSA-ARTICLE-1994-017
000059626 970__ $$aISI:A1994PU27700004/LGSA
000059626 973__ $$aEPFL$$rREVIEWED$$sPUBLISHED
000059626 980__ $$aARTICLE