Reactions of 3-O-acetyl-2-C-ρ-tolylsulfonyl-D-arabino- and -D-ribo-hex-1-enitol derivatives with nucleophiles; the SN2′ mechanism is proved firstly in glycal derivatives

DOI: 10.1016/S0040-4039(00)97461-6

Source and publish data:

Tetrahedron Letters p. 3749 - 3752 (1990)

Update date:2022-08-05

Topics:

Authors:

Sakakibara, Tohru

Takaib, Izumi

Yamamotok, Azuma

Iizuka, Hiroyuki

Hirasawa, Kohji

Ishido, Yoshiharu

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Article abstract of DOI:10.1016/S0040-4039(00)97461-6

Reactions of the title compounds with sodium methoxide and sodium borodeuteride were found to proceed mainly via the S_N2′ mechanism; nucleophiles selectively attacked the anomeric carbon atom from the same side of the leaving acetoxyl group at C-3.

Full text of DOI:10.1016/S0040-4039(00)97461-6

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