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A Simple Procedure for the Synthesis of Carbohydrate Ortholactones (1993)

Žagar, Cyrill ; Scharf, Hans-Dieter

Weinheim : Wiley-Blackwell

Liebigs Annalen 1993 (1993), S. 447-449

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ISSN: 0170-2041

Keywords: Orthoesters ; Aldonolactones ; Sugars, deoxy ; Oxonium salts ; Carbohydrates ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 3,4-Di-O-benzyl-2,6-dideoxy-L-arabino-hexono-1,5-lactone (1b) was synthesized in three steps by starting from di-O-acetyl-L-rhamnal (6). Sequential treatment of 1b or 3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hexono-1,5-lactone (1a) with triethyloxonium tetrafluoroborate and sodium ethanolate produced the diethyl ortholactones 2a and b. Acid-catalyzed reaction of 2a or b with 1,2-ethanediol (5a) or (1S,2S)-1,2-cyclohexanediol (5b) gave the spiro ortholactones 3a, b, and 4a, b.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199319930174

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