The title compounds were synthesized (as methyl glycosides) starting from 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-beta-D-glucopyranose. Stereoselective methods of glycosylation gave, via the tri-O-acetylglycopyranosyl bromide, the methyl 2-deoxy-2-fluoro-alpha- and -beta-D-glucopyranoside triacetates. Each anomer was O-deacetylated and further transformed into the corresponding, 4,6-O-benzylidenated 3-triflate, and the triflates were converted by azide displacement into the 3-azido-2,3-dideoxy-2-fluoroglycosides having the D-allo configuration. Hanesssian-Hullar reaction then furnished the corresponding 6-bromo-6-deoxy-4-benzoates, which were dehydrobrominated to give the methyl 3-azido-4-O-benzoyl-2,3,6-tri-deoxy-2-fluoro-alpha- and -beta-D-ribo-hex-5-enopyranosides. Debenzoylation of the alpha-anomer, followed by catalytic hydrogenation, led to methyl 3-amino-2,3,6-trideoxy-2-fluoro-beta-L-talopyranoside [methyl (R)-2-fluoro-beta-L-daunosaminide], whereas the same sequence applied to the beta-anomer afforded methyl 3-amino-2,3,6-trideoxy-2-fluoro-beta-D-allopyranoside [methyl (R)-2-fluoro-beta-D-ristosaminide]. The overall yields for these 10-step sequences were 11-12 and 16%, respectively. The 1H- and 13C-n.m.r. data for the new fluoro sugar derivatives are discussed with respect to the dependence of JF,H and JF,C values on molecular geometry and substituent effects.

中文翻译：

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3-氨基-2,3,6-三苯氧基-2-氟-L-塔洛糖和-D-阿洛糖[（R）-2-氟-L-豆胺和（R）-2-氟-D-香豆胺的合成]。

从1,3,4,6-四-O-乙酰基-2-脱氧-2-氟-β-D-吡喃葡萄糖开始合成标题化合物（作为甲基糖苷）。糖基化的立体选择性方法，通过三-O-乙酰基葡糖基糖基溴化物，得到2-脱氧-2-氟-α-和-β-D-吡喃葡萄糖苷三乙酸甲酯。将每个端基异构体进行O-去乙酰化，然后进一步转化为相应的4,6-O-苄基化的3-三氟甲磺酸酯，然后通过叠氮化物置换将三氟甲磺酸酯转化为具有D的3-azido-2,3-dideoxy-2-fluoroglycosides -allo配置。然后通过Hanesssian-Hullar反应得到相应的6-溴6-脱氧-4-苯甲酸酯，将其脱氢溴化，得到3-叠氮基-4-O-苯甲酰基-2,3,6-三-脱氧-2-氟甲基-alpha-和-beta-D-ribo-hex-5-enopyranosides。α-端基异构体的脱苯甲酰化，然后催化氢化，导致甲基3-氨基-2,3,6-三苯氧基-2-氟-β-L-talopyranoside[甲基（R）-2-氟-β-L-柔红酰胺]，而相同的序列适用于β-异构体得到甲基3-氨基-2,3,6-三苯氧基-2-氟-β-D-吡喃果糖苷[甲基（R）-2-氟-β-D-杀螨酰胺]。这些10步序列的总产率分别为11-12％和16％。关于JF，H和JF，C值对分子几何形状和取代基效应的依赖性，讨论了新的氟糖衍生物的1H-和13C-nmr数据。这些10步序列的总产率分别为11-12％和16％。关于JF，H和JF，C值对分子几何形状和取代基效应的依赖性，讨论了新的氟糖衍生物的1H-和13C-nmr数据。这些10步序列的总产率分别为11-12％和16％。关于JF，H和JF，C值对分子几何形状和取代基效应的依赖性，讨论了新的氟糖衍生物的1H-和13C-nmr数据。