Chemical Modification of Lactose. VIII. Studies on the Reactivities of the Secondary Hydroxyl Groups in 1,6-Anhydro-4', 6'-O-benzylidene-β-lactose by Selective p-Toluenesulfonylation
スポンサーリンク
概要
- 論文の詳細を見る
Selective tosylation of 1,6-anhydro-4', 6'-O-benzylidene-β-lactose (1), using 2.2 molar equivalents of tosyl chloride in pyridine at 0°, yielded four tosylates which were designated 2 to 5 in the order of decreasing Rf value on thin-layer chromatography. After column chromatography on silica gel, compounds 2-5 were separated as the 2,3,3'-tritosylate (2,1.3%), 2,3'-ditosylate (3,21.9%), 3'-tosylate (4,15%), and 2-tosylate (5,25.2%), respectively. Selective tosylation of 3,using 8 molar equivalents of tosyl chloride afforded 2 (29%), 15,and 16,together with 3 (15%). Compounds 15 and 16 were identified as 2,2', 3,3'-tetratosylate (15,38.9%) and 2,2', 3'-tritosylate (16,17.1%), respectively. Thus, the order of reactivities of the secondary hydroxyl groups in 1 is 2>3'>3>2'. Compounds 2-5 and 16 have potential value in the chemical modification of lactose or the syntheses of lactose-containing oligosaccharides in human milk.
- 公益社団法人日本薬学会の論文
- 1978-04-25
著者
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手島 節三
名古屋市立大学薬学部
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手島 節三
Faculty of Pharmaceutical Sciences, Nagoya City University
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高村 吏
Faculty of Pharmaceutical Sciences, Nagoya City University
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手島 節三
Faculty Of Pharmaceutical Sciences Nagoya City University
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高村 吏
Research And Development Division General Laboratory Arakawa Chotaro & Co.
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