methyl (1S,3S,4R,5R,7R,9R,11S,12S,13S)-12,13-bis(acetyloxy)-5-(6-amino-9H-purin-9-yl)-4-(benzoyloxy)-1-[(trimethylsilyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0^3,7]tridecane-11-carboxylate

Base Information

• Chemical Name: methyl (1S,3S,4R,5R,7R,9R,11S,12S,13S)-12,13-bis(acetyloxy)-5-(6-amino-9H-purin-9-yl)-4-(benzoyloxy)-1-[(trimethylsilyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0^3,7]tridecane-11-carboxylate
• CAS No.: 1391974-04-1
• Molecular Formula: C₃₁H₃₇N₅O₁₂Si
• Molecular Weight: 699.747
• Mol file: 1391974-04-1.mol

Synonyms:

Chemical Property of methyl (1S,3S,4R,5R,7R,9R,11S,12S,13S)-12,13-bis(acetyloxy)-5-(6-amino-9H-purin-9-yl)-4-(benzoyloxy)-1-[(trimethylsilyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0^3,7]tridecane-11-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1S,3S,4R,5R,7R,9R,11S,12S,13S)-12,13-bis(acetyloxy)-5-(6-amino-9H-purin-9-yl)-4-(benzoyloxy)-1-[(trimethylsilyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0^3,7]tridecane-11-carboxylate

There total 16 articles about methyl (1S,3S,4R,5R,7R,9R,11S,12S,13S)-12,13-bis(acetyloxy)-5-(6-amino-9H-purin-9-yl)-4-(benzoyloxy)-1-[(trimethylsilyl)oxy]-2,6,10-trioxatricyclo[7.4.0.0^3,7]tridecane-11-carboxylate 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: 55.0%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + methyl (1R,3S,4R,5R,7R,9R,11S,12S,13S)-5,12,13-tris(acetyloxy)-4-(benzoyloxy)-1-hydroxy-2,6,10-trioxatricyclo[7.4.0.03,7]tridecane-11-carboxylate (1391974-03-0) + adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) → methyl (1S,3S,4R,5R,7R,9R,11S,12S,13S)-12,13-bis(acetyloxy)-5-(6-amino-9H-purin-9-yl)-4-(benzoyloxy)-1-[(trimethylsilyl)oxy]-2,6,10-trioxatricyclo[7.4.0.03,7]tridecane-11-carboxylate (1391974-04-1)

Guidance literature:

In acetonitrile; at 20 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1002/anie.201201826

Reference yield: 55.0%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + methyl (1R,3S,4R,7R,9R,11S,12S,13S)-5,12,13-tris(acetyloxy)-4-(benzoyloxy)-1-hydroxy-2,6,10-trioxatricyclo[7.4.0.03,7]tridecane-11-carboxylate + adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) → methyl (1S,3S,4R,5R,7R,9R,11S,12S,13S)-12,13-bis(acetyloxy)-5-(6-amino-9H-purin-9-yl)-4-(benzoyloxy)-1-[(trimethylsilyl)oxy]-2,6,10-trioxatricyclo[7.4.0.03,7]tridecane-11-carboxylate (1391974-04-1)

Guidance literature:

In acetonitrile; at 20 ℃; for 0.0833333h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/jo401706r

Reference yield:

methyl (4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolane-4-carboxylate (1391973-92-4) → methyl (1S,3S,4R,5R,7R,9R,11S,12S,13S)-12,13-bis(acetyloxy)-5-(6-amino-9H-purin-9-yl)-4-(benzoyloxy)-1-[(trimethylsilyl)oxy]-2,6,10-trioxatricyclo[7.4.0.03,7]tridecane-11-carboxylate (1391974-04-1)

Guidance literature:

Multi-step reaction with 16 steps

1: lithium hydroxide monohydrate; water / tetrahydrofuran / 0.58 h / 20 °C / Inert atmosphere

2: dichloromethane / 1 h / 20 °C / Inert atmosphere

3: dichloromethane / 4 h / 20 °C / Inert atmosphere

4: tetrahydrofuran / 0.67 h / 10 - 20 °C / Inert atmosphere

5: borane-dimethyl sulfide complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.5 h / 30 °C / Inert atmosphere

6: dmap; triethylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere

7: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

8: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 5.5 h / 20 °C / Inert atmosphere

9: methanol; hexane; toluene / 1 h / 20 °C / Inert atmosphere

10: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

11: trifluoroacetic acid / dichloromethane; water / 0.25 h / 20 °C / Inert atmosphere

12: dimethylsulfide; ozone / dichloromethane / 3 h / -78 - 20 °C

13: dmap; triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

14: 20 wt.% Pd(OH)2 on activated carbon; hydrogen / ethyl acetate / 20 h / 20 °C / 6000.6 Torr

15: dmap; triethylamine / dichloromethane / 0.13 h / 20 °C / Inert atmosphere

16: acetonitrile / 0.08 h / 20 °C / Inert atmosphere

With dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; borane-dimethyl sulfide complex; lithium hydroxide monohydrate; dimethylsulfide; [bis(acetoxy)iodo]benzene; 20 wt.% Pd(OH)2 on activated carbon; tetrabutyl ammonium fluoride; water; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; ozone; triethylamine; trifluoroacetic acid; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; toluene; acetonitrile;

DOI:10.1002/anie.201201826

upstream raw materials:

methyl (4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolane-4-carboxylate

1-[(4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-one

(1S)-1-[(4R,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol

methyl (2S,3S,4R,5S,6R)-6-{[(4R,5S)-5-[(1S)-1-(benzoyloxy)prop-2-en-1-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-3,4-bis(benzyloxy)-5-hydroxyoxane-2-carboxylate

Downstream raw materials:

herbicidin C

aureonuclemycin