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Synthesis of methyl 5,6-dideoxy-2,3-O-isopropylidene-α-l-lyxo-hex-5-enofuranoside by G.Chaves O.; A.H. Haines is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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Treatment of methyl 2,3-O-isopropylidene-5-O-tosyI-a-L-rhamnofuranoside (1) with aqueous, methanolic potassium hydroxide was reportedlS2 to yield an olefin and a little of the parent alcohol 2. The oleCn was not completely identified and was assumed' to be the terminal olefin 3. More recently, Arzoumanian and his co-0 0 -./ CMe2 1 R=Ts 3 4 2 R=H workers3, reasoning by analogy with the conversion of methyl 6-deoxy-2,3-0isopropyhdene-5-0-tosyl-/II-D-allofuranoside into methyl 5,6-dideoxy-2,3-O-isopropylidene-B-D-erythro-hex4enofuranoside (4), suggested that the unsaturated product obtained from sulphonate I in the original workIS was, in fact, the olefin 4. As supporting evidence, the sirniiarity of the optical rotations of the products from the two reactions was cited. In spite of the fact that the experimental value for the rotation of oIefin 4 was almost immediately corrected% the suggested formation of 4 through the treatment of sulphonate 1 with base has been reiterated in at least two review articIe@. We now describe the preparation and characterization of the hitherto unknown methyl 5,6-dideoxy-2,3-O-isopropylidene-cr-L-lyoside (3) and supporting data on the properties of olef

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Author

G.Chaves O.; A.H. Haines

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)

Published

1972

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)