1-(5-O-(4,4'-dimethoxytrityl)-3-O-(triethylsilyl)-3-C-(1-hydroxy-2,2-dimethylpropyl)-2-deoxy-β-D-threo-pentofuranosyl)thymine

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Chemical Name:1-(5-O-(4,4'-dimethoxytrityl)-3-O-(triethylsilyl)-3-C-(1-hydroxy-2,2-dimethylpropyl)-2-deoxy-β-D-threo-pentofuranosyl)thymine
CAS No.:220928-47-2
Molecular Formula:C₄₂H₅₆N₂O₈Si
Molecular Weight:745.001
Hs Code.:

Synonyms:1-(5-O-(4,4'-dimethoxytrityl)-3-O-(triethylsilyl)-3-C-(1-hydroxy-2,2-dimethylpropyl)-2-deoxy-β-D-threo-pentofuranosyl)thymine

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Chemical Property of 1-(5-O-(4,4'-dimethoxytrityl)-3-O-(triethylsilyl)-3-C-(1-hydroxy-2,2-dimethylpropyl)-2-deoxy-β-D-threo-pentofuranosyl)thymine

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Technology Process of 1-(5-O-(4,4'-dimethoxytrityl)-3-O-(triethylsilyl)-3-C-(1-hydroxy-2,2-dimethylpropyl)-2-deoxy-β-D-threo-pentofuranosyl)thymine

There total 4 articles about 1-(5-O-(4,4'-dimethoxytrityl)-3-O-(triethylsilyl)-3-C-(1-hydroxy-2,2-dimethylpropyl)-2-deoxy-β-D-threo-pentofuranosyl)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: 93.0%

: 594-19-4
tert.-butyl lithium

: 220928-46-1
1-(5-O-(4,4'-dimethoxytrityl)-3-O-(triethylsilyl)-3-C-formyl-2-deoxy-β-D-threo-pentofuranosyl)thymine

: 220928-47-2
1-(5-O-(4,4'-dimethoxytrityl)-3-O-(triethylsilyl)-3-C-(1-hydroxy-2,2-dimethylpropyl)-2-deoxy-β-D-threo-pentofuranosyl)thymine

Guidance literature:: With cerium(III) chloride; In tetrahydrofuran; pentane; at -78 ℃; for 3h;
DOI:10.1021/jo982022y

Reference yield:

: 154468-74-3
5'-O-(4,4'-dimethoxytrityl)-3'-C-(hydroxymethyl)thymidine

: 220928-47-2
1-(5-O-(4,4'-dimethoxytrityl)-3-O-(triethylsilyl)-3-C-(1-hydroxy-2,2-dimethylpropyl)-2-deoxy-β-D-threo-pentofuranosyl)thymine

Guidance literature:: Multi-step reaction with 4 steps

1: 72 percent / imidazole / dimethylformamide / 24 h / 25 °C

2: 77 percent / HF, pyridine / tetrahydrofuran / 7 h / 0 °C

3: 98 percent / TPAP, NMO, 4 Angstroems MS / CH₂Cl₂ / 1 h

4: 93 percent / CeCl₃ / tetrahydrofuran; pentane / 3 h / -78 °C

With pyridine; 1H-imidazole; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; 4 Angstroems MS; hydrogen fluoride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/jo982022y

Reference yield:

: 220928-45-0
1-(5-O-(4,4'-dimethoxytrityl)-3-O-(triethylsilyl)-3-C-(hydroxymethyl)-2-deoxy-β-D-threo-pentofuranosyl)thymine

: 220928-47-2
1-(5-O-(4,4'-dimethoxytrityl)-3-O-(triethylsilyl)-3-C-(1-hydroxy-2,2-dimethylpropyl)-2-deoxy-β-D-threo-pentofuranosyl)thymine

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / TPAP, NMO, 4 Angstroems MS / CH₂Cl₂ / 1 h

2: 93 percent / CeCl₃ / tetrahydrofuran; pentane / 3 h / -78 °C

With N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; 4 Angstroems MS; In tetrahydrofuran; dichloromethane; pentane;
DOI:10.1021/jo982022y