Claisen rearrangements of 5,6-dideoxy-1,2-o-isopropylidene-.ALPHA.-D-xylo- and .ALPHA.-D-ribo-hept-5-eno-1,4-furanoses with triethyl orthoacetate.
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概要
- 論文の詳細を見る
The (<I>E</I>)- and (<I>Z</I>)-isomers (<B>2E</B> and <B>2Z</B>) of 3-<I>O</I>-benzyl-5,6-dideoxy-1,2-<I>O</I>-isopropylidene-α -D-<I>xylo</I>-hept-5-eno-1,4-furanose were subjected to Claisen rearrangement with triethyl orthoacetate. Possible two diastereomers were obtained as a 1 to 1 mixture from both of <B>2Z</B> and <B>2E</B>, and also from their 3-hydroxy or 3-siloxy derivatives. On the other hand, the rearrangement of the corresponding D-ribo derivative (<B>13Z</B>) and its 3-<I>O</I>-(<I>t</I>-butyldiphenylsilyl) derivative proceeded with a high level of diastereoselectivity. By contrast, the (<I>E</I>)-isomer of <B>13Z</B> showed no significant stereoselectivity, resulting in the formation of a diastereomeric mixture. The configurations of the introduced stereogenic centers by the rearrangements were unambiguously established by chemical transformations.
- 公益社団法人 日本化学会の論文
著者
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Ogawa Seiichiro
Department Of Applied Cemistry Faculty Of Science And Technology Keio University
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Ishihara Jun
Department Of Chemistry Faculty Of Science Hokkaido University
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Tadano Kin-ichi
Department Of Applied Chemistry Faculty Of Science And Technology Keio University
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Miyake Akiko
Department of Applied Chemistry, Faculty of Science and Technology, Keio University
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Shimada Kei-ichi
Department of Applied Chemistry, Faculty of Science and Technology, Keio University
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Ishihara Jun
Department of Applied Chemistry, Faculty of Science and Technology, Keio University
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