- Stereoselective synthesis of a C-glycosylic compound (a "methyl C-glycoside") through a regioselective free-radical ring-opening reaction. A single-crystal X-ray structure determination
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Readily available 3,4,6-tri-O-acetyl-D-glucal was converted to 2,6-anhydro-5,7-O-benzylidene-1,3,4-trideoxy-D-arabino-hept-3-enitol, a methyl C-glycosylic compound. Cyclopropanation of 4,6-O-benzylidene-D-glucal, followed by tributylstannyl radical-mediated regioselective ring opening of the 1,2-cyclopropano sugar led to a 2,6-anhydro-1-deoxyheptose, (a "methyl C-β-D-glycoside"). The stereochemistry of the 1,2-cyclopropano sugar and the "methyl C-glycoside" were confirmed by single-crystal X-ray diffraction studies.
- Shanmugasundaram, Bhagavathy,Varghese, Babu,Balasubramanian, Kalpattu K
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p. 1523 - 1527
(2007/10/03)
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- Anti-viral guanidino-substituted compounds
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Novel guanidino-substituted compounds are described having the following general formula (I): STR1 in which X may be carbon, oxygen, nitrogen or sulfur; R1 may be H, OH, linear or branched lower alkyl, lower alkoxy, lower (alkyl-substituted alk
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- REACTION OF BUTYLLITHIUM WITH BENZYLIDENE ACETALS OF ALDOPYRANOSIDES AND 1,5-ANHYDROALDITOLS
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Under suitable conditions, butyllithium selectively cleaves 5-membered benzylidene acetals (1,3-dioxolane ring) leaving the 6-membered analogs (1,3-dioxane ring) intact in aldopyranoside and 1,5-anhydroalditol derivatives.The usual course of the reaction
- Horton, Derek,Weckerle, Wolfgang
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p. 305 - 312
(2007/10/02)
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