6-(1,2-diacetoxyethyl)-1-[5-O-(4,4'-dimethoxytrityl)-2-O-methyl-β-D-ribo-furanosyl]-4-ethoxy-2-pyrimidinone

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Chemical Name:6-(1,2-diacetoxyethyl)-1-[5-O-(4,4'-dimethoxytrityl)-2-O-methyl-β-D-ribo-furanosyl]-4-ethoxy-2-pyrimidinone
CAS No.:259823-16-0
Molecular Formula:C₃₉H₄₄N₂O₁₂
Molecular Weight:732.785
Hs Code.:

Synonyms:6-(1,2-diacetoxyethyl)-1-[5-O-(4,4'-dimethoxytrityl)-2-O-methyl-β-D-ribo-furanosyl]-4-ethoxy-2-pyrimidinone

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Chemical Property of 6-(1,2-diacetoxyethyl)-1-[5-O-(4,4'-dimethoxytrityl)-2-O-methyl-β-D-ribo-furanosyl]-4-ethoxy-2-pyrimidinone

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Technology Process of 6-(1,2-diacetoxyethyl)-1-[5-O-(4,4'-dimethoxytrityl)-2-O-methyl-β-D-ribo-furanosyl]-4-ethoxy-2-pyrimidinone

There total 9 articles about 6-(1,2-diacetoxyethyl)-1-[5-O-(4,4'-dimethoxytrityl)-2-O-methyl-β-D-ribo-furanosyl]-4-ethoxy-2-pyrimidinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 3736-77-4
2,2'-Anhydrouridine

: 259823-16-0
6-(1,2-diacetoxyethyl)-1-[5-O-(4,4'-dimethoxytrityl)-2-O-methyl-β-D-ribo-furanosyl]-4-ethoxy-2-pyrimidinone

Guidance literature:: Multi-step reaction with 10 steps

1.1: 92 percent / B(OCH₃)3; Na₂CO₃ / methanol / 140 - 150 °C

2.1: 93 percent / pyridine / 6 h / 20 °C

3.1: SOCl₂ / dimethylformamide; CHCl₃ / 6 h / Heating

3.2: 83 percent / 0.5 h / 20 °C

4.1: 75 percent / imidazole / dimethylformamide / 8 h / 20 °C

5.1: LDA / tetrahydrofuran / 0.25 h / -78 °C

5.2: 87 percent / I₂ / tetrahydrofuran / 0.5 h / -78 °C

6.1: 74 percent / Pd(CH₃CN)2Cl₂ / tetrahydrofuran / 20 °C

7.1: 84 percent / NMO; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 42 h / 20 °C

8.1: 50 mg / DMAP / CH₂Cl₂ / 4 h / 20 °C

9.1: 1.44 g / TBAF*nH₂O; AcOH / tetrahydrofuran / 20 °C

10.1: 80 percent / pyridine / 2 h / 20 °C

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; thionyl chloride; N-methyl-2-indolinone; Trimethyl borate; tetrabutyl ammonium fluoride; sodium carbonate; acetic acid; lithium diisopropyl amide; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 1.1: Ring cleavage / 2.1: Acetylation / 3.1: Substitution / 3.2: Substitution / 4.1: Substitution / 5.1: Metallation / 5.2: Substitution / 6.1: Stille coupling / 7.1: dihydroxylation / 8.1: Acetylation / 9.1: Hydrolysis / 10.1: tritylation;
DOI:10.1080/07328319908044640

Reference yield:

: 2140-76-3
2'-O-methyluridine

: 259823-16-0
6-(1,2-diacetoxyethyl)-1-[5-O-(4,4'-dimethoxytrityl)-2-O-methyl-β-D-ribo-furanosyl]-4-ethoxy-2-pyrimidinone

Guidance literature:: Multi-step reaction with 9 steps

1.1: 93 percent / pyridine / 6 h / 20 °C

2.1: SOCl₂ / dimethylformamide; CHCl₃ / 6 h / Heating

2.2: 83 percent / 0.5 h / 20 °C

3.1: 75 percent / imidazole / dimethylformamide / 8 h / 20 °C

4.1: LDA / tetrahydrofuran / 0.25 h / -78 °C

4.2: 87 percent / I₂ / tetrahydrofuran / 0.5 h / -78 °C

5.1: 74 percent / Pd(CH₃CN)2Cl₂ / tetrahydrofuran / 20 °C

6.1: 84 percent / NMO; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 42 h / 20 °C

7.1: 50 mg / DMAP / CH₂Cl₂ / 4 h / 20 °C

8.1: 1.44 g / TBAF*nH₂O; AcOH / tetrahydrofuran / 20 °C

9.1: 80 percent / pyridine / 2 h / 20 °C

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; thionyl chloride; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; acetic acid; lithium diisopropyl amide; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 1.1: Acetylation / 2.1: Substitution / 2.2: Substitution / 3.1: Substitution / 4.1: Metallation / 4.2: Substitution / 5.1: Stille coupling / 6.1: dihydroxylation / 7.1: Acetylation / 8.1: Hydrolysis / 9.1: tritylation;
DOI:10.1080/07328319908044640

Reference yield:

: 259823-18-2
4-ethoxy-1-(2-O-methyl-β-D-ribofuranosyl)-2-pyrimidinone

: 259823-16-0
6-(1,2-diacetoxyethyl)-1-[5-O-(4,4'-dimethoxytrityl)-2-O-methyl-β-D-ribo-furanosyl]-4-ethoxy-2-pyrimidinone

Guidance literature:: Multi-step reaction with 7 steps

1.1: 75 percent / imidazole / dimethylformamide / 8 h / 20 °C

2.1: LDA / tetrahydrofuran / 0.25 h / -78 °C

2.2: 87 percent / I₂ / tetrahydrofuran / 0.5 h / -78 °C

3.1: 74 percent / Pd(CH₃CN)2Cl₂ / tetrahydrofuran / 20 °C

4.1: 84 percent / NMO; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 42 h / 20 °C

5.1: 50 mg / DMAP / CH₂Cl₂ / 4 h / 20 °C

6.1: 1.44 g / TBAF*nH₂O; AcOH / tetrahydrofuran / 20 °C

7.1: 80 percent / pyridine / 2 h / 20 °C

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; acetic acid; lithium diisopropyl amide; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 1.1: Substitution / 2.1: Metallation / 2.2: Substitution / 3.1: Stille coupling / 4.1: dihydroxylation / 5.1: Acetylation / 6.1: Hydrolysis / 7.1: tritylation;
DOI:10.1080/07328319908044640