(2R,5R,7R,9S,10S)-7-guanin-9-yl-5-benzyloxy-2-phenylhexahydrobenzo[1.3]dioxine

Base Information

• Chemical Name: (2R,5R,7R,9S,10S)-7-guanin-9-yl-5-benzyloxy-2-phenylhexahydrobenzo[1.3]dioxine
• CAS No.: 205681-14-7
• Molecular Formula: C₂₆H₂₆ClN₅O₃
• Molecular Weight: 491.977
• Mol file: 205681-14-7.mol

Synonyms:(2R,5R,7R,9S,10S)-7-guanin-9-yl-5-benzyloxy-2-phenylhexahydrobenzo[1.3]dioxine

Chemical Property of (2R,5R,7R,9S,10S)-7-guanin-9-yl-5-benzyloxy-2-phenylhexahydrobenzo[1.3]dioxine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5R,7R,9S,10S)-7-guanin-9-yl-5-benzyloxy-2-phenylhexahydrobenzo[1.3]dioxine

There total 17 articles about (2R,5R,7R,9S,10S)-7-guanin-9-yl-5-benzyloxy-2-phenylhexahydrobenzo[1.3]dioxine 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: 37.0%

2-Amino-6-chloropurin (10310-21-1) + (2R,5R,7S,9S,10S)-5-benzyloxy-2-phenylhexahydrobenzo[1.3]dioxin-7-ol (205681-10-3) → (2R,5R,7R,9S,10S)-7-guanin-9-yl-5-benzyloxy-2-phenylhexahydrobenzo[1.3]dioxine (205681-14-7)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; at 20 ℃;

DOI:10.1021/jo972285c

Reference yield:

(1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one (36616-60-1) → (2R,5R,7R,9S,10S)-7-guanin-9-yl-5-benzyloxy-2-phenylhexahydrobenzo[1.3]dioxine (205681-14-7)

Guidance literature:

Multi-step reaction with 15 steps

1.1: L-Selectride / tetrahydrofuran / -70 - -65 °C

2.1: 39.52 g / imidazole / dimethylformamide / 20 °C

3.1: 83 percent / KIO₄ / OsO₄ / tetrahydrofuran; H₂O / 48 h / 20 °C

4.1: 73 percent / m-CPBA / CHCl₃; aq. phosphate buffer / 0 - 20 °C / pH 8

5.1: 73 percent / K₂CO₃ / methanol / 12 h / 20 °C

6.1: 80 percent / imidazole / dimethylformamide / 20 °C

7.1: 100 percent / 2,2,6,6-tetramethylpiperidine; n-BuLi; Et₂AlCl / benzene; hexane; toluene / 3 h / 0 °C

8.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

8.2: tetrabutylammonium iodide / tetrahydrofuran / 20 °C

9.1: 9-BBN / tetrahydrofuran / 0 - 20 °C

9.2: 5.5 g / aq. NaOH; H₂O₂ / tetrahydrofuran; ethanol / 23 h / 0 - 20 °C

10.1: 93 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

11.1: 90 percent / p-toluenesulfonic acid monohydrate / dioxane / 24 h / 20 °C

12.1: 93 percent / TBAF / tetrahydrofuran / 20 °C

13.1: 2.3 g / DEAD; PPh₃ / dioxane / 20 °C

14.1: 1.24 g / K₂CO₃ / methanol; tetrahydrofuran / 20 °C

15.1: 37 percent / PPh₃; DEAD / dioxane / 20 °C

With 2,2,6,6-tetramethyl-piperidine; 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; potassium metaperiodate; tetrabutyl ammonium fluoride; diethylaluminium chloride; L-Selectride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; phosphate buffer; hexane; chloroform; water; N,N-dimethyl-formamide; toluene; benzene; 1.1: Reduction / 2.1: silylation / 3.1: Oxidation / 4.1: Baeyer-Villiger reaction / 5.1: Deacetylation / 6.1: silylation / 7.1: Ring cleavage / 8.1: Metallation / 8.2: Etherification / 9.1: Addition / 9.2: Oxidation / 10.1: desilylation / 11.1: Cyclization / 12.1: desilylation / 13.1: Mitsunobu reaction / 14.1: Hydrolysis / 15.1: Mitsunobu reaction;

DOI:10.1021/jo972285c

Reference yield:

(1S,2S,4S,6R)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-ol (35692-59-2) → (2R,5R,7R,9S,10S)-7-guanin-9-yl-5-benzyloxy-2-phenylhexahydrobenzo[1.3]dioxine (205681-14-7)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 39.52 g / imidazole / dimethylformamide / 20 °C

2.1: 83 percent / KIO₄ / OsO₄ / tetrahydrofuran; H₂O / 48 h / 20 °C

3.1: 73 percent / m-CPBA / CHCl₃; aq. phosphate buffer / 0 - 20 °C / pH 8

4.1: 73 percent / K₂CO₃ / methanol / 12 h / 20 °C

5.1: 80 percent / imidazole / dimethylformamide / 20 °C

6.1: 100 percent / 2,2,6,6-tetramethylpiperidine; n-BuLi; Et₂AlCl / benzene; hexane; toluene / 3 h / 0 °C

7.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

7.2: tetrabutylammonium iodide / tetrahydrofuran / 20 °C

8.1: 9-BBN / tetrahydrofuran / 0 - 20 °C

8.2: 5.5 g / aq. NaOH; H₂O₂ / tetrahydrofuran; ethanol / 23 h / 0 - 20 °C

9.1: 93 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

10.1: 90 percent / p-toluenesulfonic acid monohydrate / dioxane / 24 h / 20 °C

11.1: 93 percent / TBAF / tetrahydrofuran / 20 °C

12.1: 2.3 g / DEAD; PPh₃ / dioxane / 20 °C

13.1: 1.24 g / K₂CO₃ / methanol; tetrahydrofuran / 20 °C

14.1: 37 percent / PPh₃; DEAD / dioxane / 20 °C

With 2,2,6,6-tetramethyl-piperidine; 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; potassium metaperiodate; tetrabutyl ammonium fluoride; diethylaluminium chloride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; phosphate buffer; hexane; chloroform; water; N,N-dimethyl-formamide; toluene; benzene; 1.1: silylation / 2.1: Oxidation / 3.1: Baeyer-Villiger reaction / 4.1: Deacetylation / 5.1: silylation / 6.1: Ring cleavage / 7.1: Metallation / 7.2: Etherification / 8.1: Addition / 8.2: Oxidation / 9.1: desilylation / 10.1: Cyclization / 11.1: desilylation / 12.1: Mitsunobu reaction / 13.1: Hydrolysis / 14.1: Mitsunobu reaction;

DOI:10.1021/jo972285c

upstream raw materials:

2-Amino-6-chloropurin

(2R,5R,7S,9S,10S)-5-benzyloxy-2-phenylhexahydrobenzo[1.3]dioxin-7-ol

(1S,2S,4S,6R)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-ol

(1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one

Downstream raw materials:

(1S,2R,3R,5S)-5-guanin-9-yl-3-benzyloxy-2-(hydroxymethyl)cyclohexanol