The use of silyl groups in protecting the hydroxyl functions of ribonucleosides

Ogilvie, Kelvin K.; Sadana, Krishan L.; Thompson, Elaine A.; Quilliam, Michael A.; Westmore, John B.

doi:10.1016/s0040-4039(01)91763-0

Cited by 119 publications

(55 citation statements)

References 3 publications

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“…The 2'-O-isomer migrated faster as it was found in other cases [24]. The structure of the regioisomers 5a, b and 6a, b was confirmed by 'H-NMR, I3C-NMR, and NOE difference spectroscopy (Tables 1 and 2).…”

supporting

confidence: 56%

7‐Deazaadenosine: Oligoribonucleotide building block synthesis and autocatalytic hydrolysis of base‐modified hammerhead ribozymes

Seela

Mersmann

Grasby

et al. 1993

Helvetica Chimica Acta

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A 7-deazaadenosine ( = tubercidin; c'A; 1) building block for solid-phase oligoribonucleotide synthesis was prepared. The amino group of 1 was protected with the (dimethy1amino)methylidene residue (+ 3), and the monomethoxytrityl group was introduced at OH-C(5') (+4). Protection of OH-C(2') was carried out by silylation, showing that use ofthe (i-Pr)$i group resulted in high 2'-0-selectivity (+ 5b, 80%). Reaction of5b with PC1, afforded the phosphonate 7 which was used in solid-phase oligoribonucleotide synthesis. The autocatalytic hydrolysis of hammerhead ribozymes using pG-

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supporting

confidence: 56%

7‐Deazaadenosine: Oligoribonucleotide building block synthesis and autocatalytic hydrolysis of base‐modified hammerhead ribozymes

Seela

Mersmann

Grasby

et al. 1993

Helvetica Chimica Acta

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“…We have previously described in detail the synthesis of all levels of silylated ribonucleosides and the general procedures for the synthesis of nucleotides up to the tetranucleotide stage (2,3,5). We 'This article also constitutes Part XI in a series on silyl protecting groups in nucleoside and nucleotide chemistry.…”

Section: Introductionmentioning

confidence: 99%

The synthesis of oligoribonucleotides VI. The synthesis of a hexadecamer by a block condensation approach

Ogilvie¹,

Nemer²

1980

Can. J. Chem.

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The synthesis of the 5′-monomethoxytrityl-2′-tert-butyldimethylsilyl-3′-levulinylribonucleosides 4 of the four major bases involved in the phosphite procedure for the synthesis of oligoribonucleotides is described along with the 2′,3′-isomeric derivatives 6. This report describes a total protection system for nucleotide units which allows for the block condensation procedure to be used for the synthesis of long chains. The procedure is illustrated by the synthesis of a hexadecauridylic acid.

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“…We have recently described the use of alkylsilyl groups, particularly tert-butyldimethylsilyl(TBDMS), for protection of hydroxyl groups of deoxynucleosides (1-3), deoxynucleotides (4), ribonucleosides (5,6), and ribonucleotides (6). The latter work has led to the developnlent of a rapid synthesis of oligoribonucleotides.…”

Section: Introductionmentioning

confidence: 99%

The synthesis of oligoribonucleotides. III. The use of silyl protecting groups in nucleoside and nucleotide chemistry. VIII

Ogilvie¹,

Schifman²,

Penney³

1979

Can. J. Chem.

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120

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The synthesis of all isomeric mono- and disilyl derivatives of cytidine, guanosine, and their N-benzoyl analogues using the tert-butyldimethylsilyl protecting group is described. These compounds and those containing a 5′-monomethoxytrityl group have been condensed via the phosphodichloridite procedure to produce nucleotides rapidly and in good yields. The synthesis of 2′–5′-linked nucleotides is described. A cautionary note is introduced in regard to the preparation of 5′-monomethoxytritylguanosine and a novel methanolysis of certain N-benzoylcytidines is mentioned.

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The use of silyl groups in protecting the hydroxyl functions of ribonucleosides

Cited by 119 publications

References 3 publications

7‐Deazaadenosine: Oligoribonucleotide building block synthesis and autocatalytic hydrolysis of base‐modified hammerhead ribozymes

7‐Deazaadenosine: Oligoribonucleotide building block synthesis and autocatalytic hydrolysis of base‐modified hammerhead ribozymes

The synthesis of oligoribonucleotides VI. The synthesis of a hexadecamer by a block condensation approach

The synthesis of oligoribonucleotides. III. The use of silyl protecting groups in nucleoside and nucleotide chemistry. VIII

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