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A slightly shorter route to carbocyclic nucleosides. Synthesis of (±)-trans-1-[2-(hydroxymethyl)cyclopentylmethyl]uracil

✍ Scribed by Lourdes Santana; Marta Teijeira; Eugenio Uriarte

Publisher
Journal of Heterocyclic Chemistry
Year
1999
Tongue
English
Weight
186 KB
Volume
36
Category
Article
ISSN
0022-152X

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✦ Synopsis

(土)-trans-1-[2-(Hydroxymethyl)cyclopentylmethyl]uracil (1) was prepared in two steps and (56 %) yield from 2-hydroxymethylcyclopentylmethylamine (7) and 3-methoxy-2-propenoylisocyanate (6). Isocyanate 6 was prepared from methyl 3-methoxy-2-propenoate in four steps and (38 %) overall yield.

📜 SIMILAR VOLUMES

ChemInform Abstract: A Slightly Shorter
ChemInform Abstract: A Slightly Shorter Route to Carbocyclic Nucleosides. Synthesis of (.+-.)-trans-1-[2-(Hydroxymethyl)cyclopentylmethyl]uracil.
✍ Lourdes Sanatana; Marta Teijeira; Eugenio Uriarte 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB 👁 2 views

A Slightly Shorter Route to Carbocyclic Nucleosides. Synthesis of (±)-trans-1-[2-(Hydroxymethyl)cyclopentylmethyl]uracil. -Nucleoside analogue (VIII) is synthesized by constructing the uracil base around the amino alcohol precursor (VI). Isocyanate (V) is equally suitable for formation of the base