Synthesis of D‐Altritol Nucleosides with a 3′‐O‐tert‐Butyldimethylsilyl Protecting Group.

Abramov, M. A.; Marchand, Arnaud; Calleja‐Marchand, Agnes; Herdewijn, Piet

doi:10.1002/chin.200432233

Cited by 4 publications

(4 citation statements)

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“…The aq layer was extracted with CH 2 Cl 2 (3 × 700 mL). The combined organic layer was dried over Na 2 SO 4 , filtered, and concentrated in vacuo to provide a crude residue of an isomeric mixture of N 7 (28) and N 9 (27) adduct, which was used for further reaction without any purification.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Synthesis of Protected Amino Hexitol Nucleosides as Building Blocks for Oligonucleotide Synthesis

Jabgunde

Patil

et al. 2018

J. Org. Chem.

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A new synthesis protocol for the preparation of hitherto unknown 1′,5′-anhydro-4′-amino-trityl/MMTr hexitol nucleosides has been developed. Key steps in the synthesis of the pyrimidine analogues (U and C) include the regioselective D-allo-hexitol oxirane and 2′,4′-anhydronucleoside ring opening by uracil and azide, respectively. A different strategy using a regioselective epoxide ring opening of D-gulooxirane, followed by a S N 2 type of azidation reaction, has been adopted for the purine analogues (A and G). These compounds can be easily converted to 6′-phosphoramidites for the solid-phase synthesis of N4′ → P6′ phosphoramidates of amino hexitol nucleic acids (AHNA).

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Synthesis of Protected Amino Hexitol Nucleosides as Building Blocks for Oligonucleotide Synthesis

Jabgunde

Patil

et al. 2018

J. Org. Chem.

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“…However, the problem of 3′→︀4′ benzoyl migration during synthesis of the protected building blocks results in difficulties for large‐scale preparation of isomerically pure phosphoramidites. Therefore, the use of the 3′‐ O ‐TBDMS protecting group in ANA oligonucleotide synthesis has also been investigated (Abramov et al, ). Although RNA can be produced using this process, the deprotection steps are much more difficult for the preparation of ANA sequences than for RNA sequences.…”

Section: Commentarymentioning

confidence: 99%

Synthesis of Altritol Nucleoside Phosphoramidites for Oligonucleotide Synthesis

Abramov

Herdewijn

2007

CP Nucleic Acid Chemistry

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This unit describes in detail the optimized preparations of altritol nucleoside phosphoramidite building blocks for oligonucleotide synthesis (aA, aG, aC, aU). D-Altritol nucleosides with adenine and uracil bases are obtained by nucleophilic opening of the epoxide ring of 1,5:2,3-dianhydro-4,6-O-benzylidene-D-allitol using the 1,8-diazabicyclo[5.4.0]undec-7-ene salts of the above-mentioned salts, while phase transfer catalysis (18-crown-6, K2CO3) is optimal for alkylation of 2-amino-6-chloropurine. The cytosine nucleoside is synthesized starting from the uracil congener. The 3'-hydroxyl function of hexitol sugar is protected with the benzoyl group.

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“…Significant attention has been paid to ultrasonic degassing in relation to gas removal from molten alloy metals in the metallurgy industry and reasonable results have been obtained. Eskin et al [11,12], Abramov [13] and Xu et al [14,15] have reported the cavitations mechanism and effects of ultrasonic melt degassing on metallic porosity and casting quality. The results have showed that ultrasound was a fast way of degassing, which could reduce the porosity and improve the quality of metals.…”

Section: Introductionmentioning

confidence: 99%

Effect of Ultrasound on SO₂ Desorption from Sodium Alkali Desulphurization Regeneration Solution

Zhang

Lü

et al. 2010

Chem Eng & Technol

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The influence of an ultrasonic field on SO 2 desorption from sodium alkali desulfurization regeneration solution was studied in this work. The SO 2 desorption experiments were carried out in the presence and absence of ultrasound at 25 kHz. The results showed that the use of ultrasound could enhance the SO 2 desorption rate from the sodium alkali desulfurization regeneration solution. By analyzing the composition of regeneration solutions with different pH values, two steps for the desorption process were proposed, both with and without ultrasound conditions, i.e., the first step was the decomposition of sulfurous acid (H 2 SO 3 ), and the second step was the decomposition of sodium bisulfite (NaHSO 3 ). Furthermore, the use of ultrasound was seen to promote the first step, while it was not seen to have a significant effect on the second step. It was also found that the decomposition of H 2 SO 3 in the first step could be considered as a gas mass transfer process from the liquid phase to the gaseous phase and the overall volumetric mass transfer coefficient, K L ·a, increased on using ultrasound compared to the value in the absence of an ultrasonic field.

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Synthesis of D‐Altritol Nucleosides with a 3′‐O‐tert‐Butyldimethylsilyl Protecting Group.

Cited by 4 publications

References 1 publication

Synthesis of Protected Amino Hexitol Nucleosides as Building Blocks for Oligonucleotide Synthesis

Synthesis of Protected Amino Hexitol Nucleosides as Building Blocks for Oligonucleotide Synthesis

Synthesis of Altritol Nucleoside Phosphoramidites for Oligonucleotide Synthesis

Effect of Ultrasound on SO₂ Desorption from Sodium Alkali Desulphurization Regeneration Solution

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Synthesis of D‐Altritol Nucleosides with a 3′‐O‐tert‐Butyldimethylsilyl Protecting Group.

Cited by 4 publications

References 1 publication

Synthesis of Protected Amino Hexitol Nucleosides as Building Blocks for Oligonucleotide Synthesis

Synthesis of Protected Amino Hexitol Nucleosides as Building Blocks for Oligonucleotide Synthesis

Synthesis of Altritol Nucleoside Phosphoramidites for Oligonucleotide Synthesis

Effect of Ultrasound on SO2 Desorption from Sodium Alkali Desulphurization Regeneration Solution

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Effect of Ultrasound on SO₂ Desorption from Sodium Alkali Desulphurization Regeneration Solution