A NEW PROCEDURE FOR THE SYNTHESIS OF AZASUGARS

被引:54
作者
LAY, L [1 ]
NICOTRA, F [1 ]
PAGANINI, A [1 ]
PANGRAZIO, C [1 ]
PANZA, L [1 ]
机构
[1] CNR,CTR STUDIO SOSTANZE ORGAN NAT,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY
关键词
D O I
10.1016/0040-4039(93)88084-V
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of the commercially available 2,3,5-tri-O-benzyl-D-arabinose with a primary amine (RNH2) affords the arabinofuranosylamine 2, which on treatment with a Grignard reagent stereoselectively gives the aminoalcohol 3. 3 is an useful precursor of azasugars: it is converted into the pyrrolidine 4 by treatment with Tf2O-Py, whereas by oxidation with PCC it affords the lactam 5 which can be reduced to the corresponding amine 6.
引用
收藏
页码:4555 / 4558
页数:4
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