Canadian Journal of Chemistry p. 69 - 74 (1994)
Update date:2022-09-26
Topics:
Wong
Fraser-Reid
Several procedures for installing a C2 alkoxy group at C2 of a hex-2-enopyranoside have been investigated. The one that is most convenient for large-scale preparation begins with a 2-keto pyranoside, which is converted into the corresponding exo methylene derivative. An S(N)2' rearrangement is effected with thionyl chloride, and the resulting primary allylic chloride is displaced with sodium benzylate.
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