THE PREPARATION OF 4,6-O-BENZYLIDENE-D-GLUCAL AND THE REACTION OF METHYLLITHIUM WITH METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-α-D-ALLOPYRANOSIDE

1966 ◽  
Vol 44 (23) ◽  
pp. 2825-2835 ◽  
Author(s):  
M. Sharma ◽  
R. K. Brown

4,6-O-Benzylidene-D-glucal has been prepared by the reaction of benzaldehyde with D-glucal. The reaction of commercial methyllithium with methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside produces the C2-methylated 1,2-unsaturated compound 4,6-O-benzylidene-1,2-didehydro-1,2-dideoxy-2-methyl-D-ribo-hexopyranose. Their structures have been proven by first-order analyses of their nuclear magnetic resonance spectra.


1965 ◽  
Vol 18 (11) ◽  
pp. 1799 ◽  
Author(s):  
TJ Batterham ◽  
KH Bell ◽  
U Weiss

The nuclear magnetic resonance spectra of codeine, isocodeine, pseudocodeine, allopseudocodeine, neopine, isoneopine, and some of their derivatives have been studied and the patterns produced by the protons on dl rings except the N-heterocyclic ring have been analysed by first-order methods. Allylic, homoallylic, and other long-range couplings have been observed. Differences in chemical shift between protons in different isomers have been explained in terms of the anisotropy of the double bond or the aromatic ring.





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