1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-hydroxyethyl)-β-D-ribofuranosyl]thymine

Base Information

Chemical Name:1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-hydroxyethyl)-β-D-ribofuranosyl]thymine
CAS No.:664333-42-0
Molecular Formula:C₃₉H₅₀N₂O₉Si
Molecular Weight:718.92
Hs Code.:

Synonyms:1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-hydroxyethyl)-β-D-ribofuranosyl]thymine

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Chemical Property of 1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-hydroxyethyl)-β-D-ribofuranosyl]thymine

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Technology Process of 1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-hydroxyethyl)-β-D-ribofuranosyl]thymine

There total 9 articles about 1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-hydroxyethyl)-β-D-ribofuranosyl]thymine 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:

: [5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetaldehyde

: 664333-42-0
1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-hydroxyethyl)-β-D-ribofuranosyl]thymine

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; water; at 20 ℃; for 12h;
DOI:10.1039/b306354b

Reference yield:

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 664333-42-0
1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-hydroxyethyl)-β-D-ribofuranosyl]thymine

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / pyridine / 12 h / 20 °C

2: 84 percent / imidazole / dimethylformamide / 12 h / 36 °C

3: aq. NaIO₄; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / 20 °C

4: 608 mg / NaBH₄ / tetrahydrofuran; H₂O / 12 h / 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; In tetrahydrofuran; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1039/b306354b

Reference yield:

: 157037-56-4
1,3,5-tri-O-benzoyl-2-oxo-α-D-erythro-pentofuranose

: 664333-42-0
1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-hydroxyethyl)-β-D-ribofuranosyl]thymine

Guidance literature:: Multi-step reaction with 8 steps

1.1: CeCl₃*7H₂O / tetrahydrofuran; diethyl ether / 2 h / -78 °C

1.2: tetrahydrofuran; diethyl ether / 2 h / -78 °C

2.1: 3.35 g / DMAP; Et₃N / CH₂Cl₂ / 12 h / 20 °C

3.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1 h / Heating

3.2: SnCl₄ / acetonitrile / 3 h / Heating

4.1: 3.71 g / ammonia / methanol / 48 h / 20 °C

5.1: 86 percent / pyridine / 12 h / 20 °C

6.1: 84 percent / imidazole / dimethylformamide / 12 h / 36 °C

7.1: aq. NaIO₄; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / 20 °C

8.1: 608 mg / NaBH₄ / tetrahydrofuran; H₂O / 12 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N,O-bis-(trimethylsilyl)-acetamide; cerium(III) chloride; ammonia; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.2: Grignard addition;
DOI:10.1039/b306354b