5,6-不饱和己呋喃糖基糖苷和5',6'-不饱和己呋喃糖基核苷。
5,6-unsaturated hexofuranosyl glycosides and 5',6'-unsaturated hexofuranosyl nucleosides.
作者信息
Lerner L M
出版信息
Carbohydr Res. 1975 Oct;44(1):13-21. doi: 10.1016/s0008-6215(00)84331-1.
Methyl 5,6-dideoxy-2,3-O-isopropylidene-alpha-D-lyxo-hex-5-enofuranoside, prepared from methyl 2,3-O-isopropylidene-5,6-di-O-methylsulfonyl-alpha-D-mannofuranoside with sodium iodide in 2-butanone, was acetolyzed and the product coupled with 6-benzamidochloromercuripurine by the titanium tetrachloride method. Removal of the N-benzoyl group with pictic acid afforded 9-(2,3-di-O-acetyl-5,6-dideoxy-beta-D-xylo-hex-5-enofuranosyl)adenine. In a similar manner, methyl 5,6-dideoxy-2,3-O-isopropylidene-alpha-L-lyxo-hex-5-enofuranoside was prepared from L-mannose and converted into 9-(2,3-di-O-acetyl-5,6-dideoxy-beta-L-xylo-hex-5-enofuranosyl)adenine, further de-esterified to give the free nucleoside. 2,3:5,6-Di-O-isopropylidene-alpha-L-mannofuranosyl chloride, prepared from L-mannose, gave 9-(2,3-O-isopropylidene-alpha-L-mannofuranosyl)adenine, hydrolyzed into 9-alpha-L-mannofuranosyladenine. Treatment with methanesulfonyl chloride gave the 5',6'-dimethanesulfonate, which gave with sodium iodide in acetone the 5',6'-unsaturated nucleoside, further hydrolyzed into 9-(5,6-dideoxy-alpha-L-lyxo-hex-5-enofuranosyl)adenine.
5,6-二脱氧-2,3-O-异亚丙基-α-D-来苏糖基-5-烯呋喃糖苷由2,3-O-异亚丙基-5,6-二-O-甲基磺酰基-α-D-甘露呋喃糖苷与碘化钠在2-丁酮中反应制得，经乙酰解后，产物通过四氯化钛法与6-苯甲酰胺基氯汞嘌呤偶联。用苦味酸除去N-苯甲酰基得到9-(2,3-二-O-乙酰基-5,6-二脱氧-β-D-木糖基-5-烯呋喃糖基)腺嘌呤。以类似方式，由L-甘露糖制备5,6-二脱氧-2,3-O-异亚丙基-α-L-来苏糖基-5-烯呋喃糖苷，并将其转化为9-(2,3-二-O-乙酰基-5,6-二脱氧-β-L-木糖基-5-烯呋喃糖基)腺嘌呤，进一步脱酯得到游离核苷。由L-甘露糖制备的2,3:5,6-二-O-异亚丙基-α-L-甘露呋喃糖基氯得到9-(2,3-O-异亚丙基-α-L-甘露呋喃糖基)腺嘌呤，水解得到9-α-L-甘露呋喃糖基腺嘌呤。用甲磺酰氯处理得到5',6'-二甲磺酸酯，其在丙酮中与碘化钠反应得到5',6'-不饱和核苷，进一步水解得到9-(5,6-二脱氧-α-L-来苏糖基-5-烯呋喃糖基)腺嘌呤。
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