Tag: M.W=550-600

Markiewicz, Wojciech T. published the artcileStudies on synthesis and structure of O-β-D-ribofuranosyl(1”→2′)ribonucleosides and oligonucleotides, Safety of N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, the publication is Nucleosides & Nucleotides (1998), 17(1-3), 411-424, database is CAplus.

Minor nucleosides found in several eukaryotic initiator tRNAs₁^Met, O-β-D-ribofuranosyl(1”→2′)adenosine and -guanosine (Ar and Gr), as well as their pyrimidine analogs, were obtained from N-protected 3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)ribonucleosides and 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose in the presence of tin tetrachloride in 1,2-dichloroethane. A crystal structure has been solved for 2′-O-ribosyluridine. The 3′-phosphoramidites of protected 2′-O-ribosylribonucleosides were prepared as the reagents for 2′-O-ribofuranosyloligonucleotides synthesis. O-β-D-Ribofuranosyl(1”→2′)adenylyl(3’→5′)guanosine (ArpG) was obtained and its structure was analyzed by NMR spectroscopy.

Nucleosides & Nucleotides published new progress about 87865-78-9. 87865-78-9 belongs to tetrahydrofurans, auxiliary class Nucleosides and Nucleotides,Nucleoside Analogues, name is N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, and the molecular formula is C26H45N5O7Si2, Safety of N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Sekine, Mitsuo published the artcileSynthesis of adenosine, guanosine and cytidine monomer building units bearing the [[2-(methylthio)phenyl]thio]methyl (MPTM) group as the 2′-hydroxyl protecting group, Computed Properties of 87865-78-9, the publication is Nucleosides & Nucleotides (1992), 11(2-4), 679-91, database is CAplus.

A new 2′-hydroxyl protecting group, [[2-(methylthio)phenyl]thio]methyl (MPTM), was introduced into the 2′-position of adenosine, guanosine and cytidine building units required for the synthesis of oligoribonucleotides.

Nucleosides & Nucleotides published new progress about 87865-78-9. 87865-78-9 belongs to tetrahydrofurans, auxiliary class Nucleosides and Nucleotides,Nucleoside Analogues, name is N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, and the molecular formula is C15H24S, Computed Properties of 87865-78-9.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Kulikova, Irina V. published the artcileEffective isomerization of 3′,5′-O-(tetraisopropyldisiloxane-1,3-di-yl)nucleosides in the presence of trimethylsilyl trifluoromethanesulfonate, Safety of N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, the publication is ARKIVOC (Gainesville, FL, United States) (2008), 158-170, database is CAplus.

Trimethylsilyl trifluoromethanesulfonate catalyze effective isomerization of 3′,5′-O-(tetraisopropyldisiloxane-1,3-di-yl)nucleosides, e.g. I, in 1,2-dichloroethane at 0°C into 2′,3′-O-(tetraisopropyldisiloxane-1,3-di-yl)-derivatives, e.g. II, which can be obtained in 55-90% yields. On the other hand 3′,5′-O-(tetraisopropyldisiloxane-1,3-di-yl) nucleosides, e.g. I, were stable in the presence of tin tetrachloride. Only in the case of uridine derivative I a substantial amount of isomerization product II was formed.

ARKIVOC (Gainesville, FL, United States) published new progress about 87865-78-9. 87865-78-9 belongs to tetrahydrofurans, auxiliary class Nucleosides and Nucleotides,Nucleoside Analogues, name is N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, and the molecular formula is C26H45N5O7Si2, Safety of N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Bobkov, Georgii V. published the artcilePhosphoramidite building blocks for efficient incorporation of 2′-O-aminoethoxy(and propoxy)methyl nucleosides into oligonucleotides, Recommanded Product: N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, the publication is Tetrahedron (2008), 64(27), 6238-6251, database is CAplus.

A simple and efficient method for the preparation of eight phosphoramidite building blocks for incorporation of 2′-O-(2-aminoethoxymethyl)ribonucleosides and 2′-O-(3-aminopropoxymethyl)ribonucleosides into synthetic oligonucleotides has been developed. The synthetic routes are maximally convergent and provide sufficient amounts of phosphoramidites for several solid-phase synthesis coupling reactions. Using acyclic derivatives, e.g., AcOCH₂CH₂OCH₂CH₂NHCOCF₃ the overall yields of phosphoramidites, e.g. I, were increased up to 50% for pyrimidine nucleosides and up to 30% for purine derivatives with substantial decrease of total reaction steps. The 2′-O-substituent was found to be stable during oligonucleotide synthesis. The resulting oligonucleotides are of particular interest for post-synthetic functionalization and conjugation.

Tetrahedron published new progress about 87865-78-9. 87865-78-9 belongs to tetrahydrofurans, auxiliary class Nucleosides and Nucleotides,Nucleoside Analogues, name is N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, and the molecular formula is C26H45N5O7Si2, Recommanded Product: N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Drenichev, M. S. published the artcileA new protocol for selective cleavage of acyl protecting groups in 2′-O-modified 3′,5′-O-(tetraisopropyldisiloxane-1,3-diyl)ribonucleosides, Safety of N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, the publication is Synthesis (2010), 3827-3834, database is CAplus.

The stability of tetraisopropyldisiloxane-1,3-diyl (TIPDS) protection in nucleosides in ammonia/amine solutions in methanol and ethanol was studied. In ammonia-methanol at ambient temperature significant partial cleavage of TIPDS was observed When ethanol was used instead of methanol this undesired side reaction was completely inhibited. It was found that com. available 8 M methylamine-ethanol solution is the reagent of choice for selective deacylation of N- or/and O-acyl protected nucleosides without notable cleavage of 3′,5′-TIPDS group. Several examples of the developed protocol for the preparation 2′-O-modified nucleosides with overall high yields are presented.

Synthesis published new progress about 87865-78-9. 87865-78-9 belongs to tetrahydrofurans, auxiliary class Nucleosides and Nucleotides,Nucleoside Analogues, name is N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, and the molecular formula is C26H45N5O7Si2, Safety of N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Featherston, Aaron L. published the artcileCatalytic asymmetric and stereo-divergent oligonucleotide synthesis, Synthetic Route of 87865-78-9, the publication is Science (Washington, DC, United States) (2021), 371(6530), 702-707, database is CAplus and MEDLINE.

We report the catalytic stereocontrolled synthesis of dinucleotides. Chiral phosphoric acid (CPA) catalysts are demonstrated to control the formation of stereogenic phosphorous centers during phosphoramidite transfer for the first time. Unprecedented levels of diastereo-divergence are also demonstrated, enabling access to either phosphite diastereomer. Notably, two different CPA scaffolds prove essential for achieving stereo-divergence: peptide-embedded phosphothreonine-derived CPAs, which reinforce and amplify the inherent substrate preference, and C₂-sym. BINOL-derived CPAs, which completely overturn this stereochem. preference. The presently reported catalytic method does not require stoichiometric activators or chiral auxiliaries and enables asym. catalysis with readily available phosphoramidites. The method was applied to the stereocontrolled synthesis of diastereomeric dinucleotides as well as cyclic dinucleotides (CDNs) which are of broad interest in immono-oncol. as agonists of the STING pathway.

Science (Washington, DC, United States) published new progress about 87865-78-9. 87865-78-9 belongs to tetrahydrofurans, auxiliary class Nucleosides and Nucleotides,Nucleoside Analogues, name is N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, and the molecular formula is C26H45N5O7Si2, Synthetic Route of 87865-78-9.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Hirao, Ichiro published the artcileSynthesis of nonadeca- and octadecaribonucleotides using the solid-phase phosphotriester with tetrahydropyranyl groups as the 2′-hydroxyl-protecting group, Category: tetrahydrofurans, the publication is Bulletin of the Chemical Society of Japan (1989), 62(6), 1995-2001, database is CAplus.

Nonadeca- and octadecaribonucleotides corresponding to the D-loop of tRNA^Phe from yeast and the leader sequence of phage f1 coat protein mRNA were synthesized by the activated phosphotriester method. Coupling yield in the synthesis of oligoribonucleotides depended on the extent of nucleosides loaded on controlled pore glass beads (CPG). N-Acyl-5′-O-dimethoxytrityl-2′-O-tetrahydropyranyl derivatives were used as fully protected ribonucleotide monomer units. The 18mer and 19mer corresponding to the D-loop did not serve as substrates for tRNA (guanosine-2′-)methyltransferase from Thermus thermophilus, but inhibited methylation of the 5′-half fragment of tRNA^Phe. This indicates that both fragments possess some affinity with the enzyme.

Bulletin of the Chemical Society of Japan published new progress about 87865-78-9. 87865-78-9 belongs to tetrahydrofurans, auxiliary class Nucleosides and Nucleotides,Nucleoside Analogues, name is N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, and the molecular formula is C26H45N5O7Si2, Category: tetrahydrofurans.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Takaku, Hiroshi published the artcileSynthesis of oligoribonucleotides by using 2′-O-(1-methyl-1-methoxy)ethyl nucleosides, HPLC of Formula: 87865-78-9, the publication is Chemistry Letters (1987), 1787-90, database is CAplus.

3′,5′-O-Tetraisopropyldisiloxanylnucleosides I (R = benzoyladenine, uridine, R¹ = H) smoothly react with 2-methoxypropene to give I [R¹ = C(OMe)Me₂] in high yields without formation of diastereoisomers. These nucleosides were used as intermediates for oligonucleotide synthesis by the phosphotriester method. The (1-methyl-1-methoxy)ethyl group was removed rapidly from oligonucleotides by acid treatment.

Chemistry Letters published new progress about 87865-78-9. 87865-78-9 belongs to tetrahydrofurans, auxiliary class Nucleosides and Nucleotides,Nucleoside Analogues, name is N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, and the molecular formula is C12H9N3O4, HPLC of Formula: 87865-78-9.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Ogawa, Takashi published the artcileSolid-phase synthesis of oligoribonucleotides using 5′-9-fluorenylmethoxycarbonyl and 2′-1-(isopropoxyl)ethyl protection, Synthetic Route of 87865-78-9, the publication is Chemistry Letters (1991), 1169-72, database is CAplus.

The 1-(isopropoxy)ethyl group has been employed for the protection of the 2′-hydroxy groups of ribonucleoside residues in the synthesis of oligoribonucleotides by the phosphoramidite approach on a solid support, using a base-labile 5′-9-fluorenylmethoxycarbonyl group.

Chemistry Letters published new progress about 87865-78-9. 87865-78-9 belongs to tetrahydrofurans, auxiliary class Nucleosides and Nucleotides,Nucleoside Analogues, name is N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, and the molecular formula is C26H45N5O7Si2, Synthetic Route of 87865-78-9.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Timoshchuk, Victor A. published the artcileImproved and Reliable Synthesis of 3′-Azido-2′,3′-dideoxyguanosine Derivatives, COA of Formula: C26H45N5O7Si2, the publication is Nucleosides, Nucleotides & Nucleic Acids (2004), 23(1 & 2), 171-181, database is CAplus and MEDLINE.

An improved synthesis of N²-protected-3′-azido-2′,3′-dideoxyguanosine is described. Deoxygenation of 2′-O-alkyl (and/or aryl) sulfonyl-5′-dimethoxytritylguanosine coupled with [1,2]-hydride shift rearrangement gave protected 9-(2-deoxythreo-pentofuranosyl)guanines. This rearrangement was accomplished in high yield with a high degree of stereoselectivity using lithium triisobutylborohydride (L-Selectride). The resulting 2-deoxythreo-pentofuranosyl derivatives were transformed into 3′-O-mesylates, which can be used for 3′-substitution. The 3′-azido nucleosides were obtained by treatment of the 3′-O-mesylates with lithium azide. This procedure is reproducible with a good overall yield.

Nucleosides, Nucleotides & Nucleic Acids published new progress about 87865-78-9. 87865-78-9 belongs to tetrahydrofurans, auxiliary class Nucleosides and Nucleotides,Nucleoside Analogues, name is N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, and the molecular formula is C17H18N2O6, COA of Formula: C26H45N5O7Si2.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem