Bent bonds (τ) and the antiperiplanar hypothesis, and the reactivity at the anomeric center in pyranosides

2016 ◽  
Vol 14 (47) ◽  
pp. 11183-11198 ◽  
Author(s):  
Jean-François Parent ◽  
Pierre Deslongchamps
Keyword(s):  
Anomeric Center ◽  
Bent Bonds

Hyperconjugation combined with the BBA hypothesis explainsC- andO-glycosylation of bicyclic pyranoside donors with an equatorial or axial C2–OBn group.

The chemistry of bent bonds

1975 ◽  
Vol 92 (1) ◽  
pp. 81-87 ◽  
Author(s):  
Paul G. Gassman ◽  
John A. Nikora
Keyword(s):  
Bent Bonds

THE SOLVOLYSIS OF THE ALPHA- AND BETA-3,4,6-TRI-O-ACETYL-D-GLUCOPYRANOSYL CHLORIDES

1955 ◽  
Vol 33 (1) ◽  
pp. 128-133 ◽  
Author(s):  
R. U. Lemieux ◽  
G. Huber
Keyword(s):  
Acetic Acid ◽  
Double Bond ◽  
Positive Charge ◽  
Main Reaction ◽  
Main Reaction Product ◽  
Double Bond Character ◽  
Ionic Reactions ◽  
Oxygen Bond ◽  
Bond Character ◽  
Anomeric Center

3,4,6-Tri-O-acetyl-β-D-glucopyranosyl chloride was found to undergo solvolysis in acetic acid to form 1,3,4,6-tetra-O-acetyl-α-D-glucopyranose as the main reaction product. The much less reactive anomeric α-chloride also appeared to undergo solvolysis with extensive inversion of the anomeric center. It is submitted that the tendencies for inversion obtained in these ionic reactions are due to the conformations imposed on the intermediate ions through distribution of the positive charge to the ring oxygen and the consequent introduction of double-bond character to the carbon-1 to ring-oxygen bond.

Chemistry of bent bonds. XLV. Norbornyne

1975 ◽  
Vol 97 (16) ◽  
pp. 4768-4770 ◽  
Author(s):  
Paul G. Gassman ◽  
Joseph J. Valcho
Keyword(s):  
Bent Bonds

Modern methods for shortening and extending the carbon chain in carbohydrates at the anomeric center

Tetrahedron ◽  
2011 ◽  
Vol 67 (46) ◽  
pp. 8825-8850 ◽  
Author(s):  
Rune Nygaard Monrad ◽  
Robert Madsen
Keyword(s):  
Carbon Chain ◽  
Modern Methods ◽  
Anomeric Center
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