ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Nucleotides. XV. Synthesis and Properties of 2′O-t-Butyldimethylsilyl-5′-O-monomethoxytritylribonucleoside-3′-phosphotriesters, Starting Materials for Oligonucleotide SynthesesThe syntheses of two types of fully blocked ribonucleoside 3′-phosphotriesters 6-14 have been achieved in excellent yields from 2′-O-t-butyldimethylsilyl-5′-O-monomethoxytrityl-ribonucleosides 1-5 by phosphorylation with 2-chloro- and 2,5-dichlorophenylphosphorodichloridate respectively and subsequent treatment by cyanoethanol to 6, 8, 10, 12 and 14 and by p-nitrophenylethanol to 7, 9, 11 and 13. These phosphotriesters are valuable starting materials for oligonucleotide syntheses due to the fact that the corresponding phosphotriesters 15-23 with free HO—C(5′) could be obtained by detritylation and the 3′-phosphodiester triethylammonium salts 24-32 by deblocking of the cyanoethyl and the 2,5-dichlorophenyl group respectively. All newly synthesized compounds have been characterized by UV.-and NMR.-spectra as well as C, H, N elementary analyses.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19810640548
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