1969
DOI: 10.1002/cber.19691021126
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Hydrazin‐Reaktionen, VI. Konkurrenz der Wolff‐Kishner‐Reduktion und ‐Fragmentierung von Methyl‐4.6‐O‐benzyliden‐3‐desoxy‐α‐D‐erythro‐hexopyranosid‐ 2‐ulose‐hydrazonen

Abstract: Methyl-4.6-0-ben~yliden-3-desoxy-cc-~-cr~~thro-hexopyranosid-2-ulose-hydrazon (1) reagiert bcim Erhitzen niit Hydrazin zu ctwa gleichen Teilen Lum Didesoxyzucker 2 und Olefinzucker 7, dessen Bildung durch die zur Fragmentierung gunstige Konfiguration im Diimid-Anion 6 erklrirt wird. Methyl-4.6-0-benzyliden-3-desoxy-~-~-erythro-hexopyranosid-2-ulose-hydrazon (11) ergibt bei Hydrazineinwirkung, wie der Mechanismus es fordert, nur das Rcduktions- WoM-Kishner-Reduktion und -Fragmentierung (D-glirco-Reihe)Setzt ma… Show more

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Cited by 8 publications
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“…Next, the effect of the anomeric linkage was probed by first studying its stereochemical requirements. Synthesis of methyl 4,6- O -benzylidene-2,3-di- O -mesyl-α- d -galactopyranoside 14 was obtained in two steps from methyl α- d -galactopyranoside, , and then reacted with sodium methoxide solution at room temperature (Scheme ). After several days a mixture of talo - ( 15 ) and gulo -epoxides ( 16 ) were isolated; the lack of further nucleophilic attack to open the epoxide could be explained by the unfavorable 1,3-diaxial-type interactions that prevent approach of the nucleophile at both the C-2 and C-3 positions.…”
Section: Resultsmentioning
confidence: 99%
“…Next, the effect of the anomeric linkage was probed by first studying its stereochemical requirements. Synthesis of methyl 4,6- O -benzylidene-2,3-di- O -mesyl-α- d -galactopyranoside 14 was obtained in two steps from methyl α- d -galactopyranoside, , and then reacted with sodium methoxide solution at room temperature (Scheme ). After several days a mixture of talo - ( 15 ) and gulo -epoxides ( 16 ) were isolated; the lack of further nucleophilic attack to open the epoxide could be explained by the unfavorable 1,3-diaxial-type interactions that prevent approach of the nucleophile at both the C-2 and C-3 positions.…”
Section: Resultsmentioning
confidence: 99%