[(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

Base Information

• Chemical Name: [(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
• CAS No.: 500018-93-9
• Molecular Formula: C₃₁H₃₈N₇O₉P
• Molecular Weight: 683.658

Synonyms:[(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

Chemical Property of [(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(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

There total 9 articles about [(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 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:

benzoyl chloride (98-88-4) + [(2S,3S,5R)-5-(6-Amino-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 (500018-92-8) → [(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 (500018-93-9)

Guidance literature:

benzoyl chloride; [(2S,3S,5R)-5-(6-Amino-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; With triethylamine; dmap; In pyridine; at 0 - 20 ℃; for 20h;

With sodium ethanolate; In tetrahydrofuran; ethanol; at 20 ℃; for 0.333333h;

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

Reference yield:

3',4'-anhydrothymidine (7481-90-5) → [(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 (500018-93-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 100 percent / BuLi; BF₃*OEt₂ / tetrahydrofuran / 5 h / -78 °C

2.1: 64 percent / PPh₃; DIAD / tetrahydrofuran / 20 h / 0 - 20 °C

3.1: 72 percent / Me₃SiCl / ethanol; CHCl₃ / 20 h / 0 - 20 °C

4.1: 50 percent / 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) / dimethylformamide / 20 h / 20 °C

5.1: DMAP / acetonitrile / 20 h / 20 °C

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

7.1: Bu₄NF (TBAF) / acetic acid; tetrahydrofuran / 20 h / 20 °C

8.1: EtONa / ethanol / 20 h / 20 °C

9.1: Et₃N / DMAP / pyridine / 20 h / 0 - 20 °C

9.2: EtONa / tetrahydrofuran; ethanol / 0.33 h / 20 °C

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

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

Reference yield:

(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 (171336-66-6) → [(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 (500018-93-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 64 percent / PPh₃; DIAD / tetrahydrofuran / 20 h / 0 - 20 °C

2.1: 72 percent / Me₃SiCl / ethanol; CHCl₃ / 20 h / 0 - 20 °C

3.1: 50 percent / 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) / dimethylformamide / 20 h / 20 °C

4.1: DMAP / acetonitrile / 20 h / 20 °C

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

6.1: Bu₄NF (TBAF) / acetic acid; tetrahydrofuran / 20 h / 20 °C

7.1: EtONa / ethanol / 20 h / 20 °C

8.1: Et₃N / DMAP / pyridine / 20 h / 0 - 20 °C

8.2: EtONa / tetrahydrofuran; ethanol / 0.33 h / 20 °C

With dmap; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium ethanolate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; dmap; In tetrahydrofuran; pyridine; ethanol; chloroform; acetic acid; 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:

benzoyl chloride

[(2S,3S,5R)-5-(6-Amino-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

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

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