3650-68-8Relevant articles and documents
Versatility of the cyclo-oxymercuriation route to 1,2,4-Trioxanes
Bloodworth,Hagen, Torsten,Johnson, Karen A.,LeNoir, Isabelle,Moussy, Chantal
, p. 635 - 638 (2007/10/03)
The versatility of the cyclo-oxymercuriation route to 1,2,4-trioxanes is illustrated by preparing with heterocyclic, unsaturated and carbohydrate substituents and by post-cyclisation modification of the substituents including oxidative cleavage of alkene and reduction, condensation and Wittig olefination of carbonyl groups.
Synthesis of sugar-glutarimide combinations
Park,Piatak,Peterson,Clark
, p. 1662 - 1665 (2007/10/02)
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CARBON-CHAIN EXTENSION THROUGH C-1 OF 2-DEOXYALDOSE DITHIOACETAL DERIVATIVES: A ROUTE TO 1,3-DIDEOXY-2-KETOSES
Horton, Derek,Markovs, Robert A.
, p. 295 - 304 (2007/10/02)
The 3,4:5,6-diisopropylidene acetal (3) of 2-deoxy-D-arabino-hexose underwent abstraction of H-1 by butyllithium in oxolane at -30 deg C; iodomethane reacted readily with the resultant anion to give the 1,3-dideoxy-2-heptulose derivative 4, and C-1 benzylation could likewise be effected.Attempted deacetonation of 4 gave mixtures, although 6,7-monodeacetonation could be achieved in high yield, affording access via glycol cleavage-reduction to the 1,3-dideoxy-2-hexulose derivative.Demercaptalation of 4 gave the acetal-protected 1,3-dideoxy-2-heptulose, which underwent methanolysis to give crystalline methyl 1,3-dideoxy- α-D-arabino-heptulopyranoside.Anions of the type derived from 3 have broad, synthetic potential for access to chainextended, 2-keto sugar derivatives of interest as metabolic intermediates, and for synthesis of deoxy analogs of such nucleoside antibiotics as psicofuranine and decoyinine.