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1,6-Anhydrofuranosen, X. Eine einfache Synthese für 1,6-Anhydro-3-desoxy-α-D-xylo-hexofuranose (1979)

Köll, Peter ; Schulz, Jürgen ; Heyns, Kurt

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 112 (1979), S. 2337-2341

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ISSN: 0009-2940

Keywords: Chemistry ; Inorganic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 1,6-Anhydrofuranoses, X. A Simple Synthesis for 1,6-Anhydro-3-deoxy-α-D-xylo-hexofuranoseTreatment of 1,6-anhydro-2,3,5-tri-O-tosyl-α-D-galactofuranose (1) with KOH in dioxane/water gives by way of cis-elimination 1,6-anhydro-3deoxy-5-O-tosyl-α-D-threo-hexofuranos-2-ulose (2) in good yield, which tends to dimerize easily in an aldol type reaction to 3. NaBH4 reduces 2 stereoselectively to 4a Removal of the tosyl group giving the title compound 4c is accomplished by sodium amalgam.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/cber.19791120641

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