Heterocycles p. 63 - 66 (1988)
Update date:2022-08-11
Topics:
Tsuda, Yoshisuke
Okuno, Yukihiro
Kanemitsu, Kimihiro
The short step and efficient synthesis of nojirimycin (1) from commercially available 1,2-isopropylidene-D-glucofuranose (2) was described.Oxidation of 2 with (Bu3Sn)2O-Br2 followed by oximation, isomerization, and stereoselective reduction gave the 5-amino derivative of gluco-configuration (6a), which was converted to nojirimycin bisulfite adduct (8) in 50percent overall isolated yield.
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