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Synthesis of Carbocyclic Homo-N-Nucleosides from Iridoids

✍ Scribed by Henrik Franzyk; Jon Holbech Rasmussen; Raffaele Antonio Mazzei; Søren Rosendal Jensen

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
144 KB
Volume
1998
Category
Article
ISSN
1434-193X

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✦ Synopsis

Two iridoid glucosides, antirrhinoside (1) and catalpol (2), reaction or by substitution of a primary triflate with the tetrabutylammonium salt of 6-iodopurine. The latter method were converted into selectively protected polysubstituted cyclopentylmethanols, which were subsequently used to was superior with regard to both ease of purification and yield. The N-9 vs. N-7 regioselectivity of the salts of different prepare carbocyclic homo-N-nucleosides (5, 6 and 14). A purine moiety was introduced either by the Mitsunobu 6-substituted purine derivatives was briefly investigated.

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✍ Raffaele Saladino; Umberto Ciambecchini; Stephen Hanessian 📂 Article 📅 2003 🏛 John Wiley and Sons 🌐 English ⚖ 118 KB

## Abstract This paper describes a new route for the synthesis of __N__‐(1′‐homo‐L‐gulitol)nucleosides and amino sugar analogues of __N__‐(1′‐homo‐L‐gulitol)nucleosides by nucleophilic epoxide ring‐opening followed by __O__‐heterocyclization of 1,2:5,6‐dianhydro‐3,4‐di‐__O__‐benzyl‐D‐mannitol and 1