14241-58-8Relevant articles and documents
Tris(trimethylsilyl)silane and diphenylsilane in the radical chain dideoxygenation of 1,6-anhydro-D-glucose: A comparative study
Barton, Derek H. R.,Jang, Doo Ok,Jaszberenyi, Joseph Cs.
, p. 6629 - 6632 (1992)
The 2,4-bis-thinocarbonate 3 of 1,6-anyhydro-D-glucose 1 can be transformed to the corresponding dideoxy compound 5 with diphenylsilane 7 as well as with tris(trimethylsilyl)silane 4 in a radical chain reaction.
Preparation of a Chiral Lactone from Leavoglucosan; a Key Intermediate for Synthesis of the Spiroacetal Moietes of the Avermectins and Milbemycins
Baker, Raymond,Boyes, R. Hugh O.,Broom, D. Mark P.,O'Mahony, Mary J.,Swain, Christopher J.
, p. 1613 - 1622 (2007/10/02)
A synthesis of two diprotected (4S,6S)-4-hydroxy-6-hudroxymethyltetrahydropyran-2-ones has been developed from laevoglucosan.Reaction of these lactones with a substituted chiral lithium acetylide followed by hydrogenation and acid-catalysed cyclisation led to formation of the spiroacetal moiety of milbemycin α1 and α3.The acetylene was prepared by resolution of racemic material obtained from reaction of lithium acetylide and cis-butene epoxide.Alternatively a stereocontrolled synthesis was developed from (S)-methyl-3-hydroxy-2-methylpropionate which involved 'chelation controlled' addition of lithium dimethylcuprate to the corresponding tetrahydropyranyloxy aldehyde.
The Chemistry of Spiroacetals. Preparation of a Chiral Disubstituted Lactone Derivative; a Key Intermediate for Synthesis of the Spiroacetal Moieties of the Avermectins and Milbemycins
Baker, Raymond,Boyes, R. Hugh O.,Broom, D. Mark P.,Devlin, J. Alastair,Swain, Christopher J.
, p. 829 - 831 (2007/10/02)
A synthesis of two diprotected (4S,6S)-4-hydroxy-6-hydroxymethyltetrahydropyran-2-ones has been developed from laevoglucosan; reaction of these lactones with a substituted lithium acetylide derivative followed by hydrogenation and acid catalysed cyclisati
