NUCLEOPHILIC DISPLACEMENT IN 1,2-5,6-DI-O-ISOPROPYLIDENE-3-O-(P-TOLYLSULFONYL)-ALPHA-D-GLUCOFURANOSE

被引:44
作者
NAYAK, UG
WHISTLER, RL
机构
[1] Department of Biochemistry, Purdue University, Lafayette
关键词
D O I
10.1021/jo01264a017
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nucleophilic displacement of the p-tolylsulfonyloxy group in the 1,2:5,6-di-0-isopropyIidene-3-0-(p-tolylsulfonyl)-α-D-glucofuranose (I) has been successfully accomplished, using sodium azide and potassium thioacetate, to give the corresponding α-D-allofuranose derivatives (II and IV). Selective hydrolysis of 3-S-acetyl-1,2:5,6-di-O-isopropylidene-3-thio-α-D-allofuranose (IV) with 50% aqueous acetic acid affords 3-S acetyl-1,2-O-isopropylidene-3-thio-α-D-allofuranose (VI), which is acetylated to give 5,6-di-O-acetyl-3-S-acetyl-1,2-O-isopropylidene- 3-thio-α-D-allofuranose (VII). Compound VII is desulfurized using Raney nickel in ethanol to give 5,6-di-O-acetyl-3-deoxy-1,2-O-isopropylidene-D-ribo-hexofuranose, which is deacetylated to give 3-deoxy-1,2-O-isopropylidene-n-nbo-hexofuranose (VIII) in an overall yield of 50% starting from 1,2:5,6-di-O-isopropylidene-an- glucofuranose. © 1969, American Chemical Society. All rights reserved.
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页码:3819 / &
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