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

Base Information

Chemical Name:1-{(3'S,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(mercaptomethyl)-β-pentofuranosyl}thymine
CAS No.:452304-72-2
Molecular Formula:C₂₇H₃₄N₂O₄SSi
Molecular Weight:510.729
Hs Code.:

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

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

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

There total 3 articles about 1-{(3'S,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(mercaptomethyl)-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: 88.0%

: 452304-71-1
1-{(3'S,4'S)-3'-C-[(acetylthio)methyl]-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-β-pentofuranosyl}thymine

: 452304-72-2
1-{(3'S,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(mercaptomethyl)-β-pentofuranosyl}thymine

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; methanol; at 0 ℃; for 1h;
DOI:10.1002/1522-2675(200209)85:9<2777::AID-HLCA2777>3.0.CO;2-1

Reference yield:

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

: 452304-72-2
1-{(3'S,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(mercaptomethyl)-β-pentofuranosyl}thymine

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / NaBH₄ / ethanol / 2 h / 20 °C

2: 62 percent / PPh₃; DIAD / tetrahydrofuran / 2 h / 0 - 20 °C

3: 88 percent / aq. NaOH / tetrahydrofuran; methanol / 1 h / 0 °C

With sodium hydroxide; sodium tetrahydroborate; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; 2: Mitsunobu reaction;
DOI:10.1002/1522-2675(200209)85:9<2777::AID-HLCA2777>3.0.CO;2-1

Reference yield:

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

: 452304-72-2
1-{(3'S,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(mercaptomethyl)-β-pentofuranosyl}thymine

Guidance literature:: Multi-step reaction with 2 steps

1: 62 percent / PPh₃; DIAD / tetrahydrofuran / 2 h / 0 - 20 °C

2: 88 percent / aq. NaOH / tetrahydrofuran; methanol / 1 h / 0 °C

With sodium hydroxide; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; methanol; 1: Mitsunobu reaction;
DOI:10.1002/1522-2675(200209)85:9<2777::AID-HLCA2777>3.0.CO;2-1