1-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}thymine

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Chemical Name:1-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}thymine
CAS No.:146557-80-4
Molecular Formula:C₂₇H₃₄N₂O₅Si
Molecular Weight:494.663
Hs Code.:

Synonyms:1-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}thymine

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Chemical Property of 1-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}thymine

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Technology Process of 1-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}thymine

There total 9 articles about 1-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-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: 100.0%

: 146557-69-9
1-[5-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-(formyl)-β-D-erythro-pentofuranosyl]thymine

: 146557-80-4
1-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}thymine

Guidance literature:: With sodium tetrahydroborate; In ethanol; at 20 ℃; for 2h;
DOI:10.1002/1522-2675(200209)85:9<2777::AID-HLCA2777>3.0.CO;2-1

Reference yield:

: 101527-40-6
5'-O-tert-butyldiphenylsilylthymidine

: 146557-80-4
1-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}thymine

Guidance literature:: Multi-step reaction with 4 steps

1: 65 percent / methyltriphenoxyphosphonium iodide / dimethylformamide / 4 h / Ambient temperature

2: AIBN / benzene / 30 h / 80 - 82 °C

3: 63.4 percent / 1.) 4-methylmorpholine N-oxide, OsO₄; 2.) NaIO₄ / dioxane; H₂O / Ambient temperature; 1.) 2 h; 2.) 3 h

4: 83 percent / NaBH₄ / aq. ethanol / 2 h / Ambient temperature

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); methyltriphenoxyphosphonium iodide; 4-methylmorpholine N-oxide; In 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; benzene;
DOI:10.1055/s-1994-25664

Reference yield:

: 5'-O-(tert-butyldiphenylsilyl)-3'-deoxy-3'-C-(2-phenylethenyl)thymidine

: 146557-80-4
1-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}thymine

Guidance literature:: Multi-step reaction with 2 steps

1.1: OsO₄; H₂O; N-methylmorpholine oxide / dioxane / 20 °C

1.2: NaIO₄ / H₂O; dioxane / 0 - 20 °C

2.1: 3.99 g / NaBH₄ / ethanol; H₂O / 2 h / 20 °C

With sodium tetrahydroborate; osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In 1,4-dioxane; ethanol; water;
DOI:10.1021/jo001699u