Benzoic acid (2R,3S,5R)-2-(2-{[(2S,3S,5R)-5-(6-amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl]-ethoxy-phosphinoyl}-ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,5R)-2-(2-{[(2S,3S,5R)-5-(6-amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl]-ethoxy-phosphinoyl}-ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• CAS No.: 500018-90-6
• Molecular Formula: C₄₇H₅₆N₇O₉PSi
• Molecular Weight: 922.062

Synonyms:

Chemical Property of Benzoic acid (2R,3S,5R)-2-(2-{[(2S,3S,5R)-5-(6-amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl]-ethoxy-phosphinoyl}-ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Chemical Property:

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Technology Process of Benzoic acid (2R,3S,5R)-2-(2-{[(2S,3S,5R)-5-(6-amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl]-ethoxy-phosphinoyl}-ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

There total 7 articles about Benzoic acid (2R,3S,5R)-2-(2-{[(2S,3S,5R)-5-(6-amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl]-ethoxy-phosphinoyl}-ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 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:

C55H62N7O11PSSi → Benzoic acid (2R,3S,5R)-2-(2-{[(2S,3S,5R)-5-(6-amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl]-ethoxy-phosphinoyl}-ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (500018-90-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 80 ℃; for 20h;

DOI:10.1002/1522-2675(200209)85:9<2777::AID-HLCA2777>3.0.CO;2-1

Reference yield:

benzoic acid (65-85-0,8013-63-6) → Benzoic acid (2R,3S,5R)-2-(2-{[(2S,3S,5R)-5-(6-amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl]-ethoxy-phosphinoyl}-ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (500018-90-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 64 percent / PPh₃; DIAD / tetrahydrofuran / 20 h / 0 - 20 °C

2: 72 percent / Me₃SiCl / ethanol; CHCl₃ / 20 h / 0 - 20 °C

3: 50 percent / 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) / dimethylformamide / 20 h / 20 °C

4: DMAP / acetonitrile / 20 h / 20 °C

5: Bu₃SnH; azobis[isobutyronitrile] (AIBN) / toluene / 20 h / 80 °C

With dmap; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tri-n-butyl-tin hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In tetrahydrofuran; ethanol; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/1522-2675(200209)85:9<2777::AID-HLCA2777>3.0.CO;2-1

Reference yield:

3',4'-anhydrothymidine (7481-90-5) → Benzoic acid (2R,3S,5R)-2-(2-{[(2S,3S,5R)-5-(6-amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl]-ethoxy-phosphinoyl}-ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (500018-90-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / BuLi; BF₃*OEt₂ / tetrahydrofuran / 5 h / -78 °C

2: 64 percent / PPh₃; DIAD / tetrahydrofuran / 20 h / 0 - 20 °C

3: 72 percent / Me₃SiCl / ethanol; CHCl₃ / 20 h / 0 - 20 °C

4: 50 percent / 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) / dimethylformamide / 20 h / 20 °C

5: DMAP / acetonitrile / 20 h / 20 °C

6: Bu₃SnH; azobis[isobutyronitrile] (AIBN) / toluene / 20 h / 80 °C

With dmap; n-butyllithium; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In tetrahydrofuran; ethanol; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/1522-2675(200209)85:9<2777::AID-HLCA2777>3.0.CO;2-1

upstream raw materials:

benzoic acid

3',4'-anhydrothymidine

Benzoic acid (2R,3S,5R)-2-(2-ethoxyphosphinoyl-ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

(1,1-Diethoxy-ethyl)-{2-[(2R,3R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-phosphinic acid ethyl ester

Downstream raw materials:

[(2S,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-ylmethyl]-{2-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-phosphinic acid ethyl ester

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