Highly stereoselective Grignard reaction of an aldopyranose: A simple synthesis of 6-deoxy-D-idose from D-xylose.
書誌事項
- 公開日
- 1980
- DOI
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- 10.1248/cpb.28.3223
- 公開者
- 公益社団法人 日本薬学会
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説明
Grignard reaction of 2, 3, 4-tri-O-benzyl-D-xylopyranose yielded a single product with very high stereoselectivity. A threo relationship of the newly created chiral center with respect to C2 was established by converting the product into the δ-lactone of D-ido configuration, then to the unsaturated lactone of threo configuration. The result made possible a stereoselective synthesis of 6-deoxy-D-idose from D-xylose in a small number of steps. Models accounting for the high stereoselectivity in the Grignard reaction of aldoses are discussed.
収録刊行物
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- ＣＨＥＭＩＣＡＬ ＆ ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ ＢＵＬＬＥＴＩＮ
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ＣＨＥＭＩＣＡＬ ＆ ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ ＢＵＬＬＥＴＩＮ 28 (11), 3223-3231, 1980
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390282679142884736
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- NII論文ID
- 110003623825
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- NII書誌ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- 本文言語コード
- en
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- データソース種別
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- JaLC
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- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可