REACTION OF O-BENZYLIDENE SUGARS WITH N-BROMOSUCCINIMIDE .3. APPLICATIONS TO SYNTHESIS OF AMINODEOXY AND DEOXY SUGARS OF BIOLOGICAL IMPORTANCE
REACTION OF O-BENZYLIDENE SUGARS WITH N-BROMOSUCCINIMIDE .3. APPLICATIONS TO SYNTHESIS OF AMINODEOXY AND DEOXY SUGARS OF BIOLOGICAL IMPORTANCE
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DOI：
10.1021/jo01256a060
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发表时间：
1969-01-01
影响因子：
3.6
通讯作者：
PLESSAS, NR
中科院分区：
文献类型：
--
作者：
HANESSIAN, S;PLESSAS, NR
在C-3上的10个潜在反应基团以及可能受到NBS开环的苄基功能。因此，基本上按照已发表的程序重复合成6，并在结晶条件下以47%的收率获得产品。用氢化铝锂还原6，得到结晶甲基4,6 -0-苄基-3-脱氧-j3- d -核糖-己糖8，可被认为是paratose9 （3,6-dideoxy-D-rií > -己糖）的方便前体。另一方面，6与NBS反应得到的糖浆在色谱上是均匀的。该物质经苯甲酰化反应得到产物7a，该产物经催化加氢反应后发生
10 potentially reactive group at C-3 as well as the benzyli-dene function which could be subjected to ring opening with NBS. Accordingly, thesynthesis of 6 was repeated essentially according to the published pro-cedure and the product was obtained in crystalline condition in 47% yield. Reduction of 6 with lithium aluminum hydride in the usual way afforded crystalline methyl 4, 6-0-benzylidene-3-deoxy-j3-D-ribo-hexopyran-oside8 which can be considered as a convenient precursor to paratose9 (3, 6-dideoxy-D-rií> o-hexose). Reaction of 6 with NBS, on the other hand, afforded a syrupy product which was chromatographically homogeneous. Benzoylation of this material gave the product 7a which, when subjected to catalytic hydrogenation, underwent