5-O-Protected (-Tr, -Sitert-BuPh 2 ) D-and L-arabinofuranoses easily available in multigram quantities were converted to (S)-and (R)-1-O-protected glycerols, respectively, via oxidation (NaIO 4 ) and reduction (NaBH 4 ). Sources of chirality in the targets are the C4 atoms in the substrates. This st
โฆ LIBER โฆ
Simple approach to O-protected deaminotunicaminyluracil
โ Scribed by Wojciech Karpiesiuk; Anna Banaszek
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 636 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4020
No coin nor oath required. For personal study only.
โฆ Synopsis
Almlrack A five-step synthesis of dcsminotanicamtnyhuacil is presented Coupling of the ylkie. gmemted from the pbosphoniam salt 4. with the akiehyde 5 afforded the undecose 6 in high yield. The key step in this syntbis was the bydroboration-oxidatiotioo reaction of the olefin 6. For this purpbse several hydroboradng reagents wae examined. The diboraneTHP reagent led to the desired deaminotunicamioe derivative 8, as the predominant product. Condensation of uodecose 8c with 1,3di-O-tfimetJ~ylsilylaracil gave the title compound.
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