𝔖 Bobbio Scriptorium
✦   LIBER   ✦

A convenient synthesis of 2′-O-acetal-N2-acyl derivatives of riboguanosine

✍ Scribed by C. H. M. Verdegaal; P. L. Jansse; J. F. M. de Rooij; G. Veeneman; J. H. van Boom

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
620 KB
Volume
100
Category
Article
ISSN
0165-0513

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The partially protected and crystalline 2′‐O‐levulinoyl‐3′5′‐O‐(tetraisopropyldisiloxane‐1,3‐diyl)guanosine derivative (4) serves as a key intermediate for the synthesis of 2′‐O‐acetal‐N^2^‐acylriboguanosines 1c. Acylation of 4 with diphenylacetic anhydride gave, after hydrazinolysis of the levulinoyl group, the N^2^‐acyl derivative 6 in high yield. Acylation of 4 with benzoyl or biphenyl‐4‐carbonyl chloride afforded the corresponding N^2^‐acyl derivatives in lower yields. Acetalization of derivatives 6 with 4‐methoxy‐5,6‐dihydro‐2__H__‐pyran, followed by the removal of the 1,1,3,3‐tetraisopropyldisiloxane‐1,3‐diyl (TIPS) group, gave the corresponding 2′‐O‐acetal‐N^2^‐acylriboguanosines 1c.

📜 SIMILAR VOLUMES

A convenient synthesis of sodium acetate
A convenient synthesis of sodium acetate-18O2
✍ C. Richard Hutchinson; Clayton T. Mabuni 📂 Article 📅 1977 🏛 John Wiley and Sons 🌐 French ⚖ 152 KB 👁 1 views

## Abstract Sodium acetate‐^18^O~2~ is synthesized by the hydrolysis of triethyl orthoacetate with water‐^18^O in 89% chemical yield with a 1.1 to 1.2‐fold dilution of the isotopic label contained in water‐^18^O.

A New Convenient Synthesis of N-Acyl-2-(
A New Convenient Synthesis of N-Acyl-2-(dimethoxyphosphoryl)glycinates.
✍ Roman Mazurkiewicz; Anna Kuznik 📂 Article 📅 2006 🏛 John Wiley and Sons ⚖ 25 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, please click on HTML or PDF.

Stereoselective reactions of N-acyl-N,O-
Stereoselective reactions of N-acyl-N,O-acetals with 2-(trimethysilyloxy)furan
✍ Kenn E. Harding; M. Todd Coleman; Lee T. Liu 📂 Article 📅 1991 🏛 Elsevier Science 🌐 French ⚖ 262 KB

Reaction of ocyclrc chtral N-acyl-N,O-metals with 2-(aanethylsr~ylo~)~~~n and EF, Et20 produces 4-(nartnoalkyl)-2-bnten-4-ali~,~ in 3070 to 6270 y&d and vnrinbla dmrtermmeric excesses of the syn (tftrro) stereoisomer. Selectivity is dependent on the structure ofN-ncyl-N,O-metal used.

A convenient synthesis of 2-acyl-6-amino
A convenient synthesis of 2-acyl-6-aminofulvenes from cyclopentadiene
✍ Tamotsu Fujisawa; Kunikazu Sakai 📂 Article 📅 1976 🏛 Elsevier Science 🌐 French ⚖ 150 KB

Several biologically active natural products have a structure with vicinally dialkylated five-membered carbocycles: prostaqlandins, 1 pyrethroids,2 brefeldin A,3 jasmonoids,4 and so on. Cyclopentadiene is the most simple and reactive five membered carbocyclic compound and is considered to be suitabl

A convenient synthesis of 2,4-diaminoqui
A convenient synthesis of 2,4-diaminoquinoline derivatives
✍ Simon F. Campbell; J.David Hardstone; Michael J. Palmer 📂 Article 📅 1984 🏛 Elsevier Science 🌐 French ⚖ 195 KB

Base or Lewis acid induced cyclisation of the o-amidinobenzonitriles (III) provides 2,4-diaminoquinoline derivatives (IV) in high yield.