Journal of the Chemical Society. Perkin transactions I p. 2328 - 2334 (1981)
Update date:2022-08-03
Topics:
Guthrie, R. D.
Jenkins, Ian D.
Yamasaki, Ryohei
Skelton, Brian W.
White, Allan H.
Treatment of methyl β-D-fructofuranoside (6) with triphenylphosphine and diethyl azodicarboxylate in dimethylformamide gives a high yield of methyl 3,4-anhydro-β-D-tagatofuranoside (5); no blocking of the hydroxy-groups at C-1 and C-6 is necessary.The structure of the product was confirmed by an X-ray structural study of its 1,6-bis-O-(p-tolylsulphonyl) derivative and by an unambiguous synthesis.A similar reaction of methyl α-D-fructofuranoside yielded the 3,4-anhydro-α-D-tagatofuranoside.The reaction mechanism is discussed.
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Doi:10.1021/jo00320a027
(1981)Doi:10.1016/0022-1902(80)80444-1
(1980)Doi:10.1016/S0040-4039(00)71597-8
(1967)Doi:10.1021/jo01300a073
(1980)Doi:10.1248/cpb.31.3424
(1983)Doi:10.1016/S0008-6215(00)84679-0
(1980)
