Trifluoro-acetic acid (3R,9S,11S,13R,14S,16S)-3-(3-iodo-4-triisopropylsilanyloxy-benzyl)-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl ester

Base Information

• Chemical Name: Trifluoro-acetic acid (3R,9S,11S,13R,14S,16S)-3-(3-iodo-4-triisopropylsilanyloxy-benzyl)-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl ester
• CAS No.: 333354-26-0
• Molecular Formula: C₃₈H₆₀F₃IN₂O₇Si
• Molecular Weight: 868.889
• Mol file: 333354-26-0.mol

Synonyms:Trifluoro-acetic acid (3R,9S,11S,13R,14S,16S)-3-(3-iodo-4-triisopropylsilanyloxy-benzyl)-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl ester

Chemical Property of Trifluoro-acetic acid (3R,9S,11S,13R,14S,16S)-3-(3-iodo-4-triisopropylsilanyloxy-benzyl)-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Trifluoro-acetic acid (3R,9S,11S,13R,14S,16S)-3-(3-iodo-4-triisopropylsilanyloxy-benzyl)-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl ester

There total 29 articles about Trifluoro-acetic acid (3R,9S,11S,13R,14S,16S)-3-(3-iodo-4-triisopropylsilanyloxy-benzyl)-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-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:

(2S,4S,6R,7S,9S)-9-[(R)-2-[(2-Amino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionyloxy]-2,4,6,10-tetramethyl-7-(2,2,2-trifluoro-acetoxy)-undecanoic acid → Trifluoro-acetic acid (3R,9S,11S,13R,14S,16S)-3-(3-iodo-4-triisopropylsilanyloxy-benzyl)-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl ester (333354-26-0)

Guidance literature:

With dmap; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In dichloromethane; at 0 - 23 ℃; for 20h;

DOI:10.1021/ol0100069

Reference yield:

C18H28O2 → Trifluoro-acetic acid (3R,9S,11S,13R,14S,16S)-3-(3-iodo-4-triisopropylsilanyloxy-benzyl)-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl ester (333354-26-0)

Guidance literature:

Multi-step reaction with 22 steps

1: iodine; triphenylphosphine; imidazole / CH₂Cl₂ / 23 °C

2: 1.66 g / n-BuLi; TMEDA / diethyl ether / -78 °C

3: 747 mg / O₃; triphenylphosphine / CH₂Cl₂ / 4 h / 23 °C

4: NaH / tetrahydrofuran / 23 °C

5: 740 g / diisobutylaluminium hydride / CH₂Cl₂; various solvent(s) / -40 °C

6: 90 percent / (-)-DET; Ti(OiPr)4; TBHP / CH₂Cl₂ / 20 h / -23 °C

7: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 °C

8: 0.6 percent / benzene / 15 h / 80 °C

9: 90 percent / n-Bu₃P; formic acid; triethylamine / Pd₂(dba)3*CHCl₃ / dioxane / 10 h / 23 °C

10: triethylamine / CH₂Cl₂

11: 5.23 g / DIBAL-H / CH₂Cl₂ / -40 °C

12: 91 percent / Ti(OiPr)4; (+)-DET; TBHP / CH₂Cl₂ / -23 °C

13: triethylamine; DMAP / CH₂Cl₂ / 2 h / 0 °C

14: NaI; diisopropylethylamine / butan-2-one / 15 h / 85 °C

15: 285 mg / n-BuLi; TMEDA / diethyl ether / -78 °C

16: 84 percent / H₂ / Pd/C / tetrahydrofuran / 6 h / 23 °C

17: TPAP; NMO / CH₂Cl₂ / 1 h / 23 °C

18: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 23 °C

19: 96.6 mg / DMAP / 2-methyl-propan-2-ol / 15 h / 30 °C

20: 98 percent / DCC; DMAP / CH₂Cl₂ / 20 h / -20 °C

21: CH₂Cl₂ / 0 - 23 °C

22: BOP; DMAP / CH₂Cl₂ / 20 h / 0 - 23 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; formic acid; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; oxalyl dichloride; diethyl (2R,3R)-tartrate; N,N,N,N,-tetramethylethylenediamine; tributylphosphine; hydrogen; iodine; sodium hydride; diisobutylaluminium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; ozone; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; sodium iodide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; butanone; tert-butyl alcohol; benzene; 4: Horner-Emmons olefination / 6: Sharpless asymmetric epoxidation / 7: Swern oxidation / 8: Wittig homologation / 12: Sharpless epoxidation;

DOI:10.1021/ol0100069

Reference yield:

C18H27IO → Trifluoro-acetic acid (3R,9S,11S,13R,14S,16S)-3-(3-iodo-4-triisopropylsilanyloxy-benzyl)-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl ester (333354-26-0)

Guidance literature:

Multi-step reaction with 21 steps

1: 1.66 g / n-BuLi; TMEDA / diethyl ether / -78 °C

2: 747 mg / O₃; triphenylphosphine / CH₂Cl₂ / 4 h / 23 °C

3: NaH / tetrahydrofuran / 23 °C

4: 740 g / diisobutylaluminium hydride / CH₂Cl₂; various solvent(s) / -40 °C

5: 90 percent / (-)-DET; Ti(OiPr)4; TBHP / CH₂Cl₂ / 20 h / -23 °C

6: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 °C

7: 0.6 percent / benzene / 15 h / 80 °C

8: 90 percent / n-Bu₃P; formic acid; triethylamine / Pd₂(dba)3*CHCl₃ / dioxane / 10 h / 23 °C

9: triethylamine / CH₂Cl₂

10: 5.23 g / DIBAL-H / CH₂Cl₂ / -40 °C

11: 91 percent / Ti(OiPr)4; (+)-DET; TBHP / CH₂Cl₂ / -23 °C

12: triethylamine; DMAP / CH₂Cl₂ / 2 h / 0 °C

13: NaI; diisopropylethylamine / butan-2-one / 15 h / 85 °C

14: 285 mg / n-BuLi; TMEDA / diethyl ether / -78 °C

15: 84 percent / H₂ / Pd/C / tetrahydrofuran / 6 h / 23 °C

16: TPAP; NMO / CH₂Cl₂ / 1 h / 23 °C

17: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 23 °C

18: 96.6 mg / DMAP / 2-methyl-propan-2-ol / 15 h / 30 °C

19: 98 percent / DCC; DMAP / CH₂Cl₂ / 20 h / -20 °C

20: CH₂Cl₂ / 0 - 23 °C

21: BOP; DMAP / CH₂Cl₂ / 20 h / 0 - 23 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; formic acid; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; oxalyl dichloride; diethyl (2R,3R)-tartrate; N,N,N,N,-tetramethylethylenediamine; tributylphosphine; hydrogen; sodium hydride; diisobutylaluminium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; ozone; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; sodium iodide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; butanone; tert-butyl alcohol; benzene; 3: Horner-Emmons olefination / 5: Sharpless asymmetric epoxidation / 6: Swern oxidation / 7: Wittig homologation / 11: Sharpless epoxidation;

DOI:10.1021/ol0100069

upstream raw materials:

triisopropylsilyl chloride

methyl (R)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoate

(2S,4S,6R,7S,9S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-hydroxy-2,4,6,10-tetramethyl-undecanoic acid

(2R,4R,6S)-7-Benzyloxy-2,4,6-trimethyl-heptanal

Downstream raw materials:

(3R,9S,11S,13R,14S,16S)-14-hydroxy-3-[(4-hydroxy-3-iodophenyl)methyl]-4,9,11,13-tetramethyl-16-(propan-2-yl)-1-oxa-4,7-diazacyclohexadecane-2,5,8-trione

(3R,9S,11S,13R,14S,16S)-14-Hydroxy-3-(3-iodo-4-triisopropylsilanyloxy-benzyl)-16-isopropyl-4,9,11,13-tetramethyl-1-oxa-4,7-diaza-cyclohexadecane-2,5,8-trione