2021
DOI: 10.1055/a-1538-9883
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New Cleavable Spacers for Tandem Synthesis of Multiple Oligo­nucleotides

Abstract: In solid-phase oligonucleotide synthesis, a single oligonucleotide is generally acquired from a column loaded with a specific solid support. Herein, we have developed new cleavable spacer (CS) derivatives for tandem synthesis of multiple oligonucleotides on a single column. Four CS analogs were designed, synthesized, and inserted between two oligonucleotide sequences using an automated oligonucleotide synthesizer. The CS derivatives bearing a cyclic cis-1,2-diol exhibited efficient release of the two oligonucl… Show more

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Cited by 5 publications
(12 citation statements)
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“…Dihydroxylation using a catalytic amount of osmium tetroxide (OsO 4 ) in the presence of 4methylmorpholine N-oxide (NMO) afforded the corresponding diols 5b-d in 80-90% yields. Furthermore, the dihydroxylation of 7-oxabicyclo[2.2.1]hept-2-ene stereoselectively provided the exo-cis-glycol as the sole isomer 21 and benzo-fused 7-oxabicyclo[2.2.1]hept-2-ene (4a) was converted into solely the exo-cis-glycol 5a; 23 therefore, diols 5b-d would have the same configuration, as shown. Subsequently, the desired carboxylic acid compounds 2b-d were synthesized by DMTr protection followed by succinylation.…”
Section: Paper Synthesismentioning
confidence: 65%
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“…Dihydroxylation using a catalytic amount of osmium tetroxide (OsO 4 ) in the presence of 4methylmorpholine N-oxide (NMO) afforded the corresponding diols 5b-d in 80-90% yields. Furthermore, the dihydroxylation of 7-oxabicyclo[2.2.1]hept-2-ene stereoselectively provided the exo-cis-glycol as the sole isomer 21 and benzo-fused 7-oxabicyclo[2.2.1]hept-2-ene (4a) was converted into solely the exo-cis-glycol 5a; 23 therefore, diols 5b-d would have the same configuration, as shown. Subsequently, the desired carboxylic acid compounds 2b-d were synthesized by DMTr protection followed by succinylation.…”
Section: Paper Synthesismentioning
confidence: 65%
“…Compound 2a was synthesized from 4a via 5a according to our previous report. 23 5,8-Dimethyl-1,4-dihydro-1,4-epoxynaphthalene ( 4b ) 26 and 5,8-dimethoxy-1,4-dihydro-1,4-epoxynaphthalene ( 4c ) 27 were prepared according to the literature. 5,8-Bis(methoxymethoxy)-1,4-dihydro-1,4-epoxynaphthalene ( 4d ) was synthesized using a Diels–Alder­ reaction between a benzyne, generated from 2-bromo-1,4-bis(methoxymethoxy)benzene, 28 and furan (see the experimental section).…”
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confidence: 99%
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“…The organic phases were collected, reduced under pressure, and purified by column chromatography (10−35% EtOAc in heptane) to obtain the title compound S2 as a white foam (5.08 g, 91%). R f = 0.21 (EtOAc/Hept, 30:70); 1 H NMR (400 MHz, Acetone-d 6 ) δ 7.53− 7.15 (m, 18H, 2xDMTr), 6.90−6.81 (m, 8H, 2xDMTr), 3.77 (s, 12H, OCH3), 3.54−3.43 (m, 1H, H4), 3.07 (t, J = 6.5 Hz, 4H, H1,H7), 1.86−1.36 (m, 8H, H2,H3,H5,H6); 13 1,7-Di-O-dimethoxytrityl-heptane-4-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite (S3). 16 Compound S3 was prepared by coevaporating S2 (400 mg, 531.25 μmol) with anhydrous DCE (7 mL) and redissolved in anhydrous DCM (4 mL).…”
Section: 7-di-o-(44′-dimethoxytrityl)heptane-147-triol (S2)mentioning
confidence: 99%
“…The isomers were not isolated but found in a ratio of 0.4:0.6 (7a:7b) in the UV-trace from LC−MS and confirmed by integration of H1′ in NMR spectra. R f = 0.39 (EtOAc/Hept, 80:20); 1 H NMR (400 MHz, DMSO-d 6 ) δ 11.43 (s, 1H,NH), 7.70 (2 × d, J = 8.1 Hz, 1H, H6,7a + 7b), 7.44−7.20 (m, 9H, aromatic, 7a + 7b), 6.95−6.87 (m, 4H, aromatic, 7a + 7b), 5.92 (d, J = 4.5 Hz, 0.4H, H1′, 7a), 5.82 (d, J = 5.8 Hz, 0.6H, 2′-OH, 7b), 5.76 (d, J = 5.6 Hz, 0.6H, H1′, 7b), 5.58 (d, J = 6.2 Hz, 0.4H, 3′-OH, 7a), 5.46 (d, J = 7.9 Hz, 0.6H, H5, 7b), 5.41 (d, J = 8.0 Hz, 0.4H, H5, 7a), 5.27 (t, J = 5.1 Hz, 0.4H, H2′,7a), 5.14 (t, J = 5.1 Hz, 0.6H, H3′, 7b), 4.45−4.19 (m, 1H, H3′ 7a, H2′ 7b), 4.12 (q, J = 4.2 Hz, 0.6H, H4′, 7b), 4.01−3.97 (m, 0.4H, H4′, 7a), 3.75 (s, 6H, 2 × OCH3, 7a + 7b), 3.32−3.18 (m, 2H, H5′/H5″, 7a + 7b), 2.09 (s, 1.2H, CH3, 7a), 2.07 (s, 1.8H, CH3, 7b); 13 17 Compound S8 was prepared by co-evaporating S7 (204 mg, 340 μmol) in a dry round-bottom flask with dry DCE (7 mL) and redissolved in dry DCM (5 mL) followed by addition of 2-cyanoethyl N,N,N′,N′tetraisopropylphosphoramidite (205 mg, 216 μL, 680 μmol) and diisopropylammonium tetrazolide (116.4 mg, 680 μmol). The reaction was stirred under argon o/n.…”
Section: 7-di-o-(44′-dimethoxytrityl)heptane-147-triol (S2)mentioning
confidence: 99%