@article{oai:kanagawa-u.repo.nii.ac.jp:00002939, author = {吉村, 寿次 and Yoshimura, Juji and Mikami, Kazutoshi and 佐藤, 憲一 and Sato, Ken-ichi and 辛, 重基 and Shin, Chung-gi}, issue = {6}, journal = {Bulletin of the Chemical Society of Japan}, month = {Jun}, note = {Stereoselectivities in the Grignard, diazomethane and nitromethane reaction of methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose (1) were examined. In contrast to the Grignard reaction of 1 using methylmagnesium iodide to give a single 2-C-methyl derivative (4), the diazomethane reaction followed by reduction afforded another epimer (6). The nitromethan condensation product (10) of 1 was converted into the corresponding 2-C-acetaminomethyl derivative (13). The NMR spectrum of 2-O-acetate of 4 and comparison of the optical rotations of 4, 6, 10 and 13 in cupraramonium solution indicated that 4 and others have D-gluco-and D-manno-configuration, respectively. Discussions were made on the stereoselectivties of these reactions., Article}, pages = {1686--1689}, title = {Branched-chain Sugars. VIII. On the Configuration of Branched-chain Sugars from Methyl 3-O-Benzoyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose}, volume = {49}, year = {1976} }