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3,6-dideoxy-3,6-imino-1,2-o-isopropylidene-α-d-glucofuranose as a divergent intermediate for the synthesis of hydroxylated pyrrolidines; synthesis of 1,4 dideoxy-1,4-imino-l-gulitol, 1,4-dideoxy-i,4-imino-d-lyxitol, 2S,3S,4R-3,4-dihydroxyproline and (1S,2R,8S,8aR)-1,2,8-trihydroxyoctahydroindolizine [8-epi swainsonine]. X-ray crystal structure of (1S,2R,8S,8aR)-1,2,8-trihydroxy-5-oxo octahydroindolizine
Tetrahedron ( IF 2.1 ) Pub Date : 1987 , DOI: 10.1016/s0040-4020(01)86851-4
George W.J. Fleet , Josephine M. Peach , Paul W. Smith , Geoffrey N. Austin , Peter D. Baird , David J. Watkin

An efficient synthesis of the p-toluenesulphonate salt of 3,6-dideoxy-3,6-imino 1,2-0-isopropylidene-α-D-glucofuranose (1) from glucose is reported; the potential of (1) in making hydroxylated pyrrolidines is illustrated by the preparation of 1,4-dideoxy-1,4-imino-L-gulitol, 1,4-dideoxy-1,4-imino-D-lyxitol (a powerful α galactosidase inhibitor), 2S,3S,4R-3,4-dihydroxyproline and (1S,2R,8S,8aR)-1,2,6 trihydroxyoctahydroindolizine [8-epi-Swainsonine]. An X-ray crystal structure of (1S,2R,83,8aR)-1,2,8-trihydroxy-5-oxo-octahydroindolizine is reported.

中文翻译:

3,6-二脱氧-3,6-亚氨基-1,2-邻-异亚丙基-α-d-呋喃葡萄糖,作为发散中间体,用于合成羟基化的吡咯烷;1,4双脱氧-1,4-亚氨基-1-古洛糖醇,1,4-二脱氧-i,4-亚氨基-d-木糖醇,2S,3S,4R-3,4-二羟基脯氨酸和(1S,2R, 8S,8aR)-1,2,8-三羟基八氢吲哚嗪[8-表swainsonine]。(1S,2R,8S,8aR)-1,2,8-三羟基-5-氧代八氢吲哚嗪的X射线晶体结构

据报道由葡萄糖有效合成了3,6-二脱氧-3,6-亚氨基1,2-0-异亚丙基-α-D-葡萄糖呋喃糖(1)的对甲苯磺酸盐;(1)在制备羟基化吡咯烷中的潜力可通过制备1,4-二脱氧-1,4-亚氨基-L-古洛糖醇,1,4-二脱氧-1,4-亚氨基-D-木糖醇( α半乳糖苷酶抑制剂),2S,3S,4R-3,4-二羟基脯氨酸和(1S,2R,8S,8aR)-1,2,6三羟基八氢吲哚嗪[8-表-Swainsonine]。报道了(1S,2R,83,8aR)-1,2,8-三羟基-5-氧代-八氢吲哚嗪的X射线晶体结构。
更新日期:2017-01-31
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