STEREOSELECTIVE CONVERSION OF D-GLUCURONOLACTONE INTO PSEUDO-SUGAR - SYNTHESES OF PSEUDO-ALPHA-D-GLUCOPYRANOSE, PSEUDO-BETA-D-GLUCOPYRANOSE, AND VALIDAMINE
STEREOSELECTIVE CONVERSION OF D-GLUCURONOLACTONE INTO PSEUDO-SUGAR - SYNTHESES OF PSEUDO-ALPHA-D-GLUCOPYRANOSE, PSEUDO-BETA-D-GLUCOPYRANOSE, AND VALIDAMINE
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DOI：
10.1016/s0040-4020(01)85530-7
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发表时间：
1994-08-08
期刊：
影响因子：
2.1
通讯作者：
KITAGAWA, I
中科院分区：
文献类型：
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作者：
YOSHIKAWA, M;MURAKAMI, N;KITAGAWA, I
以D-葡萄糖醛酸内酯为原料，通过硝基甲烷加成反应和NaBH_4还原消除乙氧基乙氧基部分，以较好的总收率合成了两种光学活性假糖：假α-D-吡喃葡萄糖（12）和假β-D-吡喃葡萄糖（13）。此外，通过取代硝基环醇衍生物（14）中硝基的β-位上的乙酰氧基的反应，有效地合成了具有生物活性的假氨基糖，井冈霉胺（18），所述硝基环醇衍生物（14）由假-D-吡喃葡萄糖（12，13）的合成中间体（9）制备。
Two optically active pseudo-sugars, pseudo-alpha-D-glucopyranose (12) and pseudo-beta-D-glucopyranose (13), were synthesized from D-glucuronolactone in favorable overall yields by using a stereoselective nitromethane addition reaction and a reductive elimination of an ethoxyethoxyl moiety with NaBH4 as key steps. Furthermore, a biologically active pseudo-aminosugar, validamine (18) was efficiently synthesized via a substitution reaction for an acetoxyl group at the beta-position of nitro group in a nitrocyclitol derivative (14) which was prepared from a synthetic intermediate (9) of pseudo-D-glucopyranoses (12, 13).