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Syntheses with stable isotopes: D-glucose-6-13C AND 1,6-anhydro-β-L-idopyranose-6-13C

✍ Scribed by D. L. Williams; T. W. Whaley

Publisher
John Wiley and Sons
Year
1982
Tongue
French
Weight
430 KB
Volume
19
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The synthesis of a mixture of D‐glucose‐6‐^13^C and 1,6‐anhydro‐β‐L‐idopyranose‐6‐^13^C and their resolution by column chromatography are described. The Kiliani reaction of hydrogen cyanide‐^13^C with 5‐aldo‐1, 2‐0‐isopropylidene‐D‐xylo‐pentofuranose afforded epimeric cyanohydrins. Rapid in situ hydrolysis of the nitriles was effected at 50°C to obtain a mixture of the corresponding alduronic acids. The latter were reduced with LiAlH~4~. Hydrolysis of the isopropylidene groups with trifluoroacetic acid gave a mixture of glucose and anhydroidose. After chromatographic separation, the labeled carbohydrates were obtained in yields of 48% and 25%, respectively. Results of a ^13^C NMR study of the Kiliani cyanohydrin reaction are also reported.

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