The 2- and 3-C-Methyl Derivatives of Methyl 2,3-Dideoxy-α-D-erythro-hex-2-enopyranosid-4-ulose

1975 ◽  
Vol 53 (13) ◽  
pp. 2017-2023 ◽  
Author(s):  
David Roy Hicks ◽  
Bert Fraser-Reid

The oxirane rings of carbohydrate 2,3-anhydro sugars are opened stereospecifically by lithium dimethyl cuprate. These reactions go in high yields, without the formation of abberant side products encountered with other organometallic reagents. The alcohols produced are converted via their xanthate esters to olefins in good overall yields. The latter on hydrolysis and oxidation give the title enones.

1977 ◽  
Vol 30 (8) ◽  
pp. 1855 ◽  
Author(s):  
TG Burrowes ◽  
WR Jackson ◽  
S Faulks ◽  
I Sharp

Reaction of 5-chloromethyl-3-phenyl-4,5-dihydroisoxazole with potassium t-butoxide in dimethyl sulphoxide gives 4-phenyl-2-oxa-3- azabicyclo[3,1,0]hex-3-ene in high yield and reaction of the 5-(1?- chloroethyl) homologue gives high yields of the diastereoisomeric 6- methyl derivatives of the bicyclic system. Some unsuccessful attempts to convert these bicyclic compounds into substituted cyclo-propanols and cyclopropenes are described.


1978 ◽  
Vol 56 (24) ◽  
pp. 3087-3095 ◽  
Author(s):  
Hans H. Baer ◽  
Friedrich Linhart ◽  
Hanna R. Hanna

The methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitrohex-2-enopyranosides having the β-D-erythro (1), α-D-erythro (2), β-D-threo (3), and α-D-threo (4) configurations reacted with diazomethane to give high yields of 2,3-(1′-pyrazolino-3′,4′) derivatives (5–8). The pyrazolines 5 and 6 (from 1 and 2) were deduced on the basis of nuclear magnetic resonance and optical rotatory dispersion data to possess the β- and α-D-gluco configurations, and 7 and 8 (from 3 and 4), to have the β- and α-D-ido configurations, respectively. Thermolysis of 5, 6, and 8 led to the methyl-branched, nitroolefinic glycosides 9, 10, and 11 (the 2-C-methyl derivatives of 1, 2, and 4), whereas 7 afforded the corresponding 2,3-C-methylene derivative 12, a cyclopropano sugar. The α-anomeric cyclopropano derivative 13 was obtained from 8 by decomposition on silica gel.


1982 ◽  
Vol 85 (1) ◽  
pp. 257-263 ◽  
Author(s):  
A. Graja ◽  
M. Przybylski ◽  
B. Butka ◽  
R. Swietlik

1974 ◽  
Vol 39 (11) ◽  
pp. 3109-3116 ◽  
Author(s):  
J. Šrogl ◽  
M. Janda ◽  
I. Stibor ◽  
V. Skála ◽  
P. Trška ◽  
...  

1972 ◽  
Vol 46 (4) ◽  
pp. 1734-1741 ◽  
Author(s):  
E. Darżynkiewicz ◽  
J.T. Kuśmierek ◽  
D. Shugar

1980 ◽  
Vol 9 (6) ◽  
pp. 611-612 ◽  
Author(s):  
Akinori Hasegawa ◽  
Takatoshi Yamaguchi ◽  
Michiro Hayashi

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