Chlorination of 1,5-anhydro-4,6-O-benzylidene-2,3-dideoxy-3-nitro-D-arabino-hex-1-enitol in cyclic ethers such as tetrahydrofuran stereoselectively afforded the ω-chloroalkyl β-D-glycopyranoside derivatives, whereas in 1,4-dioxane α-D-glycopyranosyl chloride was obtained in high yield.
T. Sakakibara, Y. Nomura, K. Yoshino and R. Sudoh, J. Chem. Soc., Chem. Commun., 1983, 449 DOI: 10.1039/C39830000449
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