𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of Novel Nucleosides with a Fused Cyclopropane Ring Substituted by a Hydroxymethyl Group

✍ Scribed by Cyrille Lescop; François Huet

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
294 KB
Volume
56
Category
Article
ISSN
0040-4020

No coin nor oath required. For personal study only.

✦ Synopsis

AbstractÐThe two diastereomers of a 3-oxabicyclo[3.1.0]hexan-2-ol 21a±b with the cyclopropane ring substituted by a hydroxymethyl group were synthesized from both products 17a and 18a obtained from the bromohydroxylation of epoxide 16a derived from 3-oxabicyclo[3.2.0]hept-6-en-2-one 15. This preparation involved two stereospeci®c C 4 ±C 3 ring contractions leading to cis,cis-trisubstituted cyclopropane compounds 18a and 12. The hydroxylactols 21a±b thus obtained were diacetylated and the single product 22 was subjected to substitution at the anomeric position by protected or free bases, providing, in each case, only one of the possible products. Deprotection with ammonia yielded new bicyclic nucleosides 11a±d.

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis and Antiv
ChemInform Abstract: Synthesis and Antiviral Activity of Novel anti-VZV 5-Substituted Uracil Nucleosides with a Cyclopropane Sugar Moiety.
✍ Takashi Tsuji 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 27 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

ChemInform Abstract: Synthesis and Some
ChemInform Abstract: Synthesis and Some Transformations of Bicyclic γ-Lactones with a Fused Cyclopropane Ring.
✍ A. A. Avetisyan; G. G. Tokmadzhyan; L. V. Karapetyan; L. S. Balayan 📂 Article 📅 2009 🏛 John Wiley and Sons ⚖ 27 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

Synthesis of a novel bridged nucleoside
Synthesis of a novel bridged nucleoside bearing a fused-azetidine ring, 3′-amino-3′,4′-BNA monomer
✍ Satoshi Obika; Jyun-ichi Andoh; Mayumi Onoda; Osamu Nakagawa; Akiko Hiroto; Tomo 📂 Article 📅 2003 🏛 Elsevier Science 🌐 French ⚖ 190 KB

A novel bridged nucleic acid monomer, 3%-amino-3%-deoxy-5-methyl-3%-N,4%-C-methyleneuridine, was successfully synthesized via a useful and convenient azetidine ring formation under Staudinger's conditions. A 1 H NMR experiment and a PM3 calculation revealed that the sugar moiety of the novel bridged