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

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Chemical Name:1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(3-hydroxypropyl)-β-D-ribofuranosyl]thymine
CAS No.:664333-37-3
Molecular Formula:C₄₀H₅₂N₂O₉Si
Molecular Weight:732.946
Hs Code.:

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

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

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

There total 8 articles about 1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(3-hydroxypropyl)-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: 55.0%

: 664333-36-2
1-[2-C-allyl-3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]thymine

: 664333-37-3
1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(3-hydroxypropyl)-β-D-ribofuranosyl]thymine

Guidance literature:: 1-[2-C-allyl-3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]thymine; With borane; In tetrahydrofuran; at 20 ℃; for 12h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 2h; Further stages.;
DOI:10.1039/b306354b

Reference yield:

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

: 664333-37-3
1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(3-hydroxypropyl)-β-D-ribofuranosyl]thymine

Guidance literature:: Multi-step reaction with 3 steps

1.1: 86 percent / pyridine / 12 h / 20 °C

2.1: 84 percent / imidazole / dimethylformamide / 12 h / 36 °C

3.1: BH₃ / various solvent(s); tetrahydrofuran / 12 h / 20 °C

3.2: 55 percent / aq. NaOH; H₂O₂ / various solvent(s); tetrahydrofuran / 2 h / 20 °C

With pyridine; 1H-imidazole; borane; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1039/b306354b

Reference yield:

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

: 664333-37-3
1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(3-hydroxypropyl)-β-D-ribofuranosyl]thymine

Guidance literature:: Multi-step reaction with 7 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: BH₃ / various solvent(s); tetrahydrofuran / 12 h / 20 °C

7.2: 55 percent / aq. NaOH; H₂O₂ / various solvent(s); tetrahydrofuran / 2 h / 20 °C

With pyridine; 1H-imidazole; dmap; N,O-bis-(trimethylsilyl)-acetamide; cerium(III) chloride; borane; ammonia; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.2: Grignard addition;
DOI:10.1039/b306354b