2-N-acetyl-9-N-(2,5-di-O-acetyl-3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-β-D-ribofuranosyl)-6-O-diphenylcarbamoylguanine

Base Information

Chemical Name:2-N-acetyl-9-N-(2,5-di-O-acetyl-3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-β-D-ribofuranosyl)-6-O-diphenylcarbamoylguanine
CAS No.:482621-50-1
Molecular Formula:C₃₄H₃₇F₂N₆O₁₀PS
Molecular Weight:790.739
Hs Code.:

Synonyms:2-N-acetyl-9-N-(2,5-di-O-acetyl-3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-β-D-ribofuranosyl)-6-O-diphenylcarbamoylguanine

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Chemical Property of 2-N-acetyl-9-N-(2,5-di-O-acetyl-3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-β-D-ribofuranosyl)-6-O-diphenylcarbamoylguanine

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Technology Process of 2-N-acetyl-9-N-(2,5-di-O-acetyl-3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-β-D-ribofuranosyl)-6-O-diphenylcarbamoylguanine

There total 12 articles about 2-N-acetyl-9-N-(2,5-di-O-acetyl-3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-β-D-ribofuranosyl)-6-O-diphenylcarbamoylguanine 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: 56.0%

: 482621-42-1
1,2,3-tri-O-acetyl-3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-β-D-ribofuranose

: 112233-74-6
N₂-acetyl-O₆-(diphenylcarbamoyl)guanine

: 482621-50-1
2-N-acetyl-9-N-(2,5-di-O-acetyl-3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-β-D-ribofuranosyl)-6-O-diphenylcarbamoylguanine

Guidance literature:: N₂-acetyl-O₆-(diphenylcarbamoyl)guanine; With bis-(trimethylsilyl)acetamide; In 1,2-dichloro-ethane; for 0.0833333h; Heating;

1,2,3-tri-O-acetyl-3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-β-D-ribofuranose; With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; for 1h; Further stages.; Heating;
DOI:10.1021/ja027850u

Reference yield:

: 103931-45-9
5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose

: 482621-50-1
2-N-acetyl-9-N-(2,5-di-O-acetyl-3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-β-D-ribofuranosyl)-6-O-diphenylcarbamoylguanine

Guidance literature:: Multi-step reaction with 5 steps

1.1: tert-butyllithium / tetrahydrofuran; pentane / 0.17 h / -78 °C

1.2: 70 percent / tetrahydrofuran; pentane / -78 °C

2.1: n-BuLi / tetrahydrofuran / -78 °C

2.2: tetrahydrofuran / -78 - 0 °C

3.1: 58 percent / n-Bu₃SnH; AIBN / toluene / Heating

4.1: 59 percent / AcOH; H₂SO₄ / 20 °C

5.1: bis(trimethylsilyl)acetamide / 1,2-dichloro-ethane / 0.08 h / Heating

5.2: 56 percent / TMSOTf / 1,2-dichloro-ethane / 1 h / Heating

With n-butyllithium; 2,2'-azobis(isobutyronitrile); sulfuric acid; tert.-butyl lithium; tri-n-butyl-tin hydride; acetic acid; bis-(trimethylsilyl)acetamide; In tetrahydrofuran; 1,2-dichloro-ethane; toluene; pentane;
DOI:10.1021/ja027850u

Reference yield:

: 180627-08-1
O,O-diethyl 1,1-difluoro-1-bromomethane phosphonothioate

: 482621-50-1
2-N-acetyl-9-N-(2,5-di-O-acetyl-3-deoxy-3-(O,O-diethylphosphonothio)difluoromethyl-β-D-ribofuranosyl)-6-O-diphenylcarbamoylguanine

Guidance literature:: Multi-step reaction with 5 steps

1.1: tert-butyllithium / tetrahydrofuran; pentane / 0.17 h / -78 °C

1.2: 70 percent / tetrahydrofuran; pentane / -78 °C

2.1: n-BuLi / tetrahydrofuran / -78 °C

2.2: tetrahydrofuran / -78 - 0 °C

3.1: 58 percent / n-Bu₃SnH; AIBN / toluene / Heating

4.1: 59 percent / AcOH; H₂SO₄ / 20 °C

5.1: bis(trimethylsilyl)acetamide / 1,2-dichloro-ethane / 0.08 h / Heating

5.2: 56 percent / TMSOTf / 1,2-dichloro-ethane / 1 h / Heating

With n-butyllithium; 2,2'-azobis(isobutyronitrile); sulfuric acid; tert.-butyl lithium; tri-n-butyl-tin hydride; acetic acid; bis-(trimethylsilyl)acetamide; In tetrahydrofuran; 1,2-dichloro-ethane; toluene; pentane;
DOI:10.1021/ja027850u