Branched-chain sugars. XXI. Synthesis of new branched-chain cyclitols having neo-, myo-, and chiro-configurations from 3-O-benzyl-5,6-dideoxy-5-C-(1,3-DITHIAN-2-YL)-6-NITRO-D-galactofuranose and -L-altrofuranose.
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概要
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The Michael addition of 2-lithio-1,3-dithiane to 3-<I>O</I>-benzyl-5,6-dideoxy-1,2-<I>O</I>-isopropylidene-6-nitro-β-L-<I>arabino</I>-hex-5-enofuranose afforded a 1 : 1.8 mixture of 3-<I>O</I>-benzyl-5,6-dideoxy-5-<I>C</I>-(1,3-dithian-2-yl)-1,2-<I>O</I>-isopropylidene-6-nitro-α-D-galactofuranose and-β-L-altrofuranose. Removal of the isopropylidene group and intra-molecular cyclization under weakly basic conditions afforded a mixture of branched-chain cyclitols having <I>neo</I>-, <I>myo</I>-, and <I>chiro</I>-configuration. A similar cyclization of the <I>O</I>-deisopropylidenated product of 3-<I>O</I>-benzyl-5,6-dideoxy-1,2-<I>O</I>-isopropylidene-6-nitro-5-<I>C</I>-(nitromethyl)-β-L-<I>arabino</I>-hexofuranose also afforded a mixture of cyclitols having <I>neo</I>-, <I>myo</I>-, and <I>chiro</I>-configuration. The results confirm the importance of two bulky groups such as benzyloxy at C-3 and 1,3-dithiane residue at C-5 in determining the stereodirection of cyclization.
- 公益社団法人 日本化学会の論文
著者
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Yoshimura Juji
Laboratorium für Organische Chemie Technische Hochschule Tokyo
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Iwakawa Masaharu
Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology
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Funabash Masuo
Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology
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