Reactions of 2-hydroxy-6,8-dioxabicyclo[3.2.1]oct-3-ene with diethylaminosulfur trifluoride and with halogens. Facile synthesis of 1,6- anhydrohalohexopyranoses
D-Galactal 1 reacts in THF in the presence of catalytic amounts of concentrated sulfuric acid to give (2R)-2-hydroxy-6,8-dioxabicyclo[3.2.1]oct- 3-ene (4) in a Ferrier-type rearrangement in 40% yield. When 4 is treated with diethylaminosulfur trifluoride
Oberdorfer, Franz,Haeckel, Roland,Lauer, Gilbert
p. 201 - 206
(2007/10/03)
Clay montmorillonite in carbohydrates : Use of 'claysil' as an efficient heterogenous catalyst for the intramolecular Ferrier reactions leading to 1,6-anhydro rare saccharides
Clay montmorillonite supported silver reagent - claysil - was prepared and advantageously used in the intramolecular Ferrier reaction of 6-hydroxy glycals 1a-9c. The unsaturated sugars 13a-21c so obtained were stereoselectively hydroxylated leading to the
Sharma,Venkata Ramanaiah,Krishnudu
p. 1905 - 1908
(2007/10/02)
Synthesis of 1,6-anhydro-2,3-dideoxy-β-D-erythro- and -threo-hex-2-enopyranose from 3,4-di-O-substituted glycals by a facile intramolecular Ferrier reaction
The 1,6-anhydro-2,3-dideoxy-β-D-erythro- 7-9 and -threo-hex-2-enopyranoses 10-12 are valuable synthons for the preparation of structurally diverse natural products. This paper reports on a new, general, and efficient route to their synthesis from 3,4-di-O
Mereyala,Venkataramanaiah,Dalvoy
p. 151 - 153
(2007/10/02)
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