Efficient synthesis of d-[5-13C]ribose from d-ribose and its conversion into [5′-13C]nucleosides
✍ Scribed by Takeshi Sekine; Etsuko Kawashima; Yoshiharu Ishido
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- French
- Weight
- 185 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
The preparation of t3C-labeled ribonucleosides starting from D-[t3C~]glucose in 45% overall yield is described. The key of this short synthetic way is the dehomologation of di-O-isopropylidene hexofuranose 2 with periodic acid and NaBI-I4 that afforded stereoselectively the labeled ribofuranose deri
D-(1,5,6-13C3)Glucose (7) has been synthesized by a six-step chemical method. D-(1,2-13C2)Mannose (1) was converted to methyl D-(1,2-13C2)mannopyranosides (2), and 2 was oxidized with Pt-C and O2 to give methyl D-(1,2-13C2)mannopyranuronides (3). After purification by anion-exchange chromatography,
3, a C-10-C-13 synthetic segment of erythronolide A (lJ was enantiospecifically synthesized in sixteen steps and 8.3% overall yield from D-ribose. The successful total synthesis of erythronolide A (A), aglycone of the medicinally important 14-membered macrolide antibiotic erythromycin A, has recent
Three selectively labeled propynes were prepared either with deuterium or carbon-13 at position 3 and doubly labeled with carbon-13 at positions 1 and 2 by an alkylation reaction from the corresponding labeled or unlabeled monolithio acetylides and dimethylsulfates. Their lithiation with nBuLi gave