Ausgehend von der aus L‐Rhamnose (I) gut zugänglichen Ulose (II) wird durch elektrophile Alkylierung mit Methyliodid ausschließlich die am C‐3‐Atom verzweigte Ulose (III) erhalten.
Das Methyl-2,3: 5,6-di-O-isopropyliden-a-o-mannofuranosid (1) reagiert rnit Lithiumdiisopropylamid zur Methyl-3-desoxy-5,6-O-isopropyliden-a-~-erythro-hexofuranosid-2-ulose (2), w8hrend die 1,2-0-Isopropyliden-3,5,6-O-methylidin-cc-~-glucofuranose (3) die 6-Desoxy-1,2-O-isopropyliden-a-~-xylo-hexofuranos-5-ulose (4) liefert .
Reactions of Carbohydrate Acetals with Organolithium Compounds. -Synthesis of 3-Deoxy-a-~-erythhro-hexofuranosid-2-ulose and 6-Deoxy-a-o-xylo-hexofuranos-5-uloseMethyl 2,3 : 5,6-di-O-isopropylidene-a-~-mannofuranoside (1) reacts with lithium diisopropylamide to give the methyl 3-deoxy-5,6-O-isopropylidene-a-o-eryfhro-hexofuranosid-2-ulose (2), while l,2-O-~sopropyl~dene-3,5,6-O-methylidyne-~-~-g~ucofuranose (3) yields 6-deoxy-l,2-O-isopropylidene-a-D-xylo-hexofuranos-5-dose (4).
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.