1982
DOI: 10.1139/v82-165
|View full text |Cite
|
Sign up to set email alerts
|

New catalysts and procedures for the dimethoxytritylation and selective silylation of ribonucleosides

Abstract: Procedures have been developed for the selective formation of (a) 2′,5′-silylated ribonucleosides and (b) 3′,5′-silylated ribonucleosides. These procedures also permit the selective silylation at either the 2′- or 3′-position of dimethoxytritylated ribonucleosides. The procedures involve nitrate or perchlorate ion catalysis for selective reaction at 2′-positions and a combination of silver ion and DABCO or 4-nitropyridine N-oxide for selective reaction at the 3′-position. During the course of this work a gener… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1
1
1

Citation Types

2
110
0

Year Published

1989
1989
2002
2002

Publication Types

Select...
8

Relationship

1
7

Authors

Journals

citations
Cited by 204 publications
(112 citation statements)
references
References 9 publications
2
110
0
Order By: Relevance
“…The deletion of the purine exocyclic amino groups of the bases adenine and guanine was accomplished by the introduction of purine and hypoxanthine. The corresponding nucleosides [purine riboside (P) and inosine (I)] were converted to the phosphoramidite building blocks by standard procedures (27,28) in which the 2'-hydroxyl groups were protected as the t-butyldimethylsilyl ethers.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…The deletion of the purine exocyclic amino groups of the bases adenine and guanine was accomplished by the introduction of purine and hypoxanthine. The corresponding nucleosides [purine riboside (P) and inosine (I)] were converted to the phosphoramidite building blocks by standard procedures (27,28) in which the 2'-hydroxyl groups were protected as the t-butyldimethylsilyl ethers.…”
Section: Resultsmentioning
confidence: 99%
“…phosphinyl] derivative essentially by the procedures of Ogilvie and coworkers (27), Sung and Narang (28), and Usman and coworkers (29). * These procedures will be described in detail elsewhere.…”
Section: Methodsmentioning
confidence: 99%
“…Consequently, it was deemed necessary to mask the 4-OH with a protective dry DMF/pyridine (1:1) for 22 h at room temperature. [24] The expected 5Ј-DMTr ethers 4a, b of 4-OH-8-oxodGuo group stable under the conditions of solid-phase DNA synthesis but easily removable during the final ammonia depro-were isolated in 32% yield by silica gel chromatography.…”
Section: Full Papermentioning
confidence: 99%
“…The trimethylsilyl groups in both the guanosine and cytidine reactions were removed by brief treatment with ammonium hydroxide. The N-phenoxyacetylated compounds 2a-c were tritylated with monomethoxytrityl chloride and silylated with t-butyldimethylsilyl chloride (triisopropylsilyl chloride for guanosine) using the standard procedures (20) to give the 2'-t-butyldimethylsilyl (triisopropylsilyl for guanosine)-5'-monomethoxytrityl-N-phenoxyacetylnucleosides 3a-c. Phosphorylation of 3a-c was performed using N,N-diisopropylmethylphosphonamidic chloride, dimethylamino- Table 2. These results show that the half-lives of phenoxyacetylated nucleosides were very much less than the half-lives of the benzoylated nucleosides.…”
Section: Resultsmentioning
confidence: 99%