AZIDONITRATION OF TRI-O-ACETYL-D-GALACTAL
AZIDONITRATION OF TRI-O-ACETYL-D-GALACTAL
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DOI：
10.1139/v79-203
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发表时间：
1979-01-01
影响因子：
1.1
通讯作者：
RATCLIFFE, RM
中科院分区：
文献类型：
--
作者：
LEMIEUX, RU;RATCLIFFE, RM
3，4，6-三-O-乙酰基-D-半乳糖醛与过量的硝酸铈铵和叠氮化钠在乙腈中反应产生2-叠氮基-1-硝酸酯加成产物（53% β-半乳糖，22% α-半乳糖和8% α-半乳糖talo）和N-乙酰基-3，4，6-三-O-乙酰基-2-酸基-2-脱氧-α-水解后形成D-吡喃半乳糖胺，产率为10%。该反应产物提供了D-半乳糖胺和3，4，6-三-O-乙酰基-2-酸基-2-脱氧-α-氨基的方便来源。D-半乳糖苷卤化物。晶体β-氯化物的报道。这些糖基卤化物作为反应物用于制备2-酸基-2-脱氧-α和-β-本文报道了在氰化汞和银盐促进下的D-吡喃半乳糖苷。
Reaction of 3,4,6-tri-O-acetyl-D-galactal with excess ceric ammonium nitrate and sodium azide in acetonitrile produced 2-azido-1-nitrate addition products (53% .beta.-galacto, 22% .alpha.-galacto and 8% .alpha.-talo) and N-acetyl-3,4,6-tri-O-acetyl-2-acido-2-deoxy-.alpha.-D-galactopyranosylamine was formed, on hydrolysis, in 10% yield. The reaction product provides a convenient source of D-galactosamine and 3,4,6-tri-O-acetyl-2-acido-2-deoxy-.alpha.-D-galactopyranosyl halides. The crystalline .beta.-chloride is reported. The use of these glycosyl halides as reactants for the preparation of 2-acido-2-deoxy-.alpha. and -.beta.-D-galactopyranosides under conditions promoted by both mercuric cyanide and silver salts are reported.