Synthesis of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino- and 1,6-Anhydro-2,3,4-trideoxy-3,4-epimino-β-D-hexopyranoses and Their NMR and Infrared Spectra

2004 ◽  
Vol 69 (10) ◽  
pp. 1939-1954 ◽  
Author(s):  
Jindřich Karban ◽  
Miloš Buděšínský ◽  
Jiří Kroutil
Keyword(s):  
Infrared Spectra ◽  
Lithium Aluminium Hydride ◽  
Aziridine Ring ◽  
Hydride Reduction ◽  
Lithium Aluminium ◽  
Complete Series ◽  
Derivatives Of ◽  
Unusual Formation

A complete series of 2,3,4-trideoxy-2,3-epimino and 2,3,4-trideoxy-3,4-epimino derivatives of 1,6-anhydro-β-D-hexopyranoses were prepared by lithium aluminium hydride reduction of vicinal trans azido tosylates. Unusual formation of the aziridine ring from precursors with the trans-diequatorial arrangement of the reacting groups was observed. NMR and infrared spectra of the aziridines are discussed.

4,5-Seco-4,6-cyclosteroids. III. Observations on the course of reductive rearrangement of 6β-Bromo-4β,5-epoxy-5β-cholestan-3β-ol

1969 ◽  
Vol 22 (4) ◽  
pp. 807 ◽  
Author(s):  
DJ Collins ◽  
JJ Hobbs ◽  
RJ Rawson
Keyword(s):  
Hydrogen Bromide ◽  
High Yield ◽  
Lithium Aluminium Hydride ◽  
Experimental Conditions ◽  
Lithium Aluminium ◽  
Reaction Proceeds ◽  
Derivatives Of

It has been shown that reductive rearrangement of 6β-bromo-4β,5-epoxy- 5β-cholestan-3β-ol (I) to 4,5-seco-4,6-cycle-6β-cholestane-3β,5α-diol (IXa) with lithium aluminium hydride in tetrahydrofuran proceeds via 6β-bromo-5β-cholestane-3β,5-diol (IIa). Relevant reactions of the latter and the corresponding 3-ketone are discussed. ��� Similar conversion of the 3-epimer of (I) into 4,5-seco-4,6-cyclo- 6β-cholestane-3α,5α-diol (XIIIa) in high yield indicates that reductive rearrangement of the 6β-bromo-5β-hydroxy moiety proceeds without participation of the 3-aluminate complex. Some derivatives of (XIIIa) are described. ��� Experimental conditions required for the conversion of (I) into (IXa) are defined. ��� Combined evidence indicates that the reaction proceeds in a concerted manner by essentially base-catalysed, 1,3-elimination of hydrogen bromide from diol (IIa) with 4,5-bond migration to give the formal intermediate 3β-hydroxy-4,5-seco-4,6-cyclo-6β-cholestan-5-one (VI), further reduced to (IXa).

Lithium aluminium hydride reduction of some organo-sulphur compounds.

1967 ◽  
Vol 8 (11) ◽  
pp. 971-974 ◽  
Author(s):  
Kazi Abdul Latif ◽  
Paritosh Kumar Chakraborty
Keyword(s):  
Lithium Aluminium Hydride ◽  
Sulphur Compounds ◽  
Hydride Reduction ◽  
Lithium Aluminium

scholarly journals Lithium Aluminium Hydride Reduction of Pregnenolone under Conditions of Assumed Kinetic and Equilibrium Control.

1981 ◽  
Vol 35b ◽  
pp. 407-410 ◽  
Author(s):  
Stig Allenmark ◽  
Hans Borén ◽  
Bertil Samuelsson ◽  
Bertil Samuelsson ◽  
Ulrika Örn
Keyword(s):  
Lithium Aluminium Hydride ◽  
Hydride Reduction ◽  
Lithium Aluminium ◽  
Equilibrium Control
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