Trifluoro-acetic acid (3R,9S,11S,13R,14S,16S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-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-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl ester
• CAS No.: 160531-35-1
• Molecular Formula: C₃₅H₅₄F₃IN₂O₇Si
• Molecular Weight: 826.808
• Mol file: 160531-35-1.mol

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

There total 52 articles about Trifluoro-acetic acid (3R,9S,11S,13R,14S,16S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-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:

(S)-4-methyl-pentane-1,3-diol (16451-50-6) → Trifluoro-acetic acid (3R,9S,11S,13R,14S,16S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl ester (160531-35-1)

Guidance literature:

Multi-step reaction with 27 steps

1: 96 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 13 h / Ambient temperature

2: 1.) 60percent NaH, 2.) concd HCl / 1.) DMF, 0 deg C to room temp., 2.5 h, 2.) MeOH, THF, 30 deg C, 4 h

3: 96 percent / (COCl)2, DMSO; Et₃N / CH₂Cl₂ / -78 deg C, 20 min; -78 to 0 deg C, 0 deg C, 15 min

4: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 50 min; -78 deg C, 30 min; 0 deg C, 1 h

5: 92 percent / Me₃Al / tetrahydrofuran; toluene / -19 deg C, 2 h; -6 deg C, 2 h;

6: 96 percent / i-Pr₂NEt / 2 h / Ambient temperature

7: 91 percent / 1.0 M DIBAL / tetrahydrofuran; hexane / 0.17 h / -78 °C

8: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 1 h; -78 deg C, 30 min; 0 deg C, 1 h

9: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1.5 h, 2.) CHCl₃, Et₂O

10: 93 percent / tetrahydrofuran / 10 h / 70 °C

11: 79 percent / Bu₃SnH / toluene / 0.22 h / Heating

12: 97 percent / 1.0 M LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

13: 98 percent / DMSO, (COCl)2; Et₃N / CH₂Cl₂ / -78 °C / -78 deg C, 10 min; -78 to 0 deg C, 0 deg C, 10 min

14: 88 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 1 h; -78 deg C, 30 min; 0 deg C, 1 h

15: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1 h, 2.) CHCl₃, Et₂O

16: 94 percent / tetrahydrofuran / 5 h / 70 °C

17: 76 percent / Bu₃SnH / toluene / 0.17 h / Heating

18: 96 percent / concd HCl / methanol / 2 h / 50 °C

19: Ph₃P, 1.0 M (EtOOCN)2, p-nitrobenzoic acid / diethyl ether / 17.5 h / Ambient temperature

20: 52.0 mg / 20percent (w/w) aq. NaOH / methanol / 2 h / 45 °C

21: Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

22: K₂CO₃ / CH₂Cl₂; methanol; tetrahydrofuran; H₂O / 1 h / 40 °C

23: 98 percent / DEPC, Et₃N / dimethylformamide / 0.5 h / 0 °C

24: 95 percent / H₂ / 20percent Pd(OH)2/C / dioxane / 1.5 h / 40 °C / 760 Torr

25: 94 percent / 4-dimethylaminopyridine, DCC / CH₂Cl₂ / 2 h / -20 °C

26: CH₂Cl₂ / 3 h / Ambient temperature

27: 10 percent / Bop-Cl, Et₃N / CH₂Cl₂ / 0 to 25 deg C, 6 h; 25 deg C, 13 h

With hydrogenchloride; dmap; lithium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; dihydrogen peroxide; trimethylaluminum; tri-n-butyl-tin hydride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; diethyl dicarbonate; diethylazodicarboxylate; 4-nitro-benzoic acid; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)81206-0

Reference yield:

(S)-3-Benzyloxy-4-methyl-pentan-1-ol (160531-37-3) → Trifluoro-acetic acid (3R,9S,11S,13R,14S,16S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl ester (160531-35-1)

Guidance literature:

Multi-step reaction with 25 steps

1: 96 percent / (COCl)2, DMSO; Et₃N / CH₂Cl₂ / -78 deg C, 20 min; -78 to 0 deg C, 0 deg C, 15 min

2: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 50 min; -78 deg C, 30 min; 0 deg C, 1 h

3: 92 percent / Me₃Al / tetrahydrofuran; toluene / -19 deg C, 2 h; -6 deg C, 2 h;

4: 96 percent / i-Pr₂NEt / 2 h / Ambient temperature

5: 91 percent / 1.0 M DIBAL / tetrahydrofuran; hexane / 0.17 h / -78 °C

6: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 1 h; -78 deg C, 30 min; 0 deg C, 1 h

7: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1.5 h, 2.) CHCl₃, Et₂O

8: 93 percent / tetrahydrofuran / 10 h / 70 °C

9: 79 percent / Bu₃SnH / toluene / 0.22 h / Heating

10: 97 percent / 1.0 M LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

11: 98 percent / DMSO, (COCl)2; Et₃N / CH₂Cl₂ / -78 °C / -78 deg C, 10 min; -78 to 0 deg C, 0 deg C, 10 min

12: 88 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 1 h; -78 deg C, 30 min; 0 deg C, 1 h

13: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1 h, 2.) CHCl₃, Et₂O

14: 94 percent / tetrahydrofuran / 5 h / 70 °C

15: 76 percent / Bu₃SnH / toluene / 0.17 h / Heating

16: 96 percent / concd HCl / methanol / 2 h / 50 °C

17: Ph₃P, 1.0 M (EtOOCN)2, p-nitrobenzoic acid / diethyl ether / 17.5 h / Ambient temperature

18: 52.0 mg / 20percent (w/w) aq. NaOH / methanol / 2 h / 45 °C

19: Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

20: K₂CO₃ / CH₂Cl₂; methanol; tetrahydrofuran; H₂O / 1 h / 40 °C

21: 98 percent / DEPC, Et₃N / dimethylformamide / 0.5 h / 0 °C

22: 95 percent / H₂ / 20percent Pd(OH)2/C / dioxane / 1.5 h / 40 °C / 760 Torr

23: 94 percent / 4-dimethylaminopyridine, DCC / CH₂Cl₂ / 2 h / -20 °C

24: CH₂Cl₂ / 3 h / Ambient temperature

25: 10 percent / Bop-Cl, Et₃N / CH₂Cl₂ / 0 to 25 deg C, 6 h; 25 deg C, 13 h

With hydrogenchloride; dmap; lithium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; dihydrogen peroxide; trimethylaluminum; tri-n-butyl-tin hydride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; diethyl dicarbonate; diethylazodicarboxylate; 4-nitro-benzoic acid; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)81206-0

Reference yield:

(2S,3R,5S)-5-Benzyloxy-3-methoxymethoxy-2,6-dimethyl-heptanal (160531-17-9) → Trifluoro-acetic acid (3R,9S,11S,13R,14S,16S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl ester (160531-35-1)

Guidance literature:

Multi-step reaction with 20 steps

1: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 1 h; -78 deg C, 30 min; 0 deg C, 1 h

2: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1.5 h, 2.) CHCl₃, Et₂O

3: 93 percent / tetrahydrofuran / 10 h / 70 °C

4: 79 percent / Bu₃SnH / toluene / 0.22 h / Heating

5: 97 percent / 1.0 M LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

6: 98 percent / DMSO, (COCl)2; Et₃N / CH₂Cl₂ / -78 °C / -78 deg C, 10 min; -78 to 0 deg C, 0 deg C, 10 min

7: 88 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 1 h; -78 deg C, 30 min; 0 deg C, 1 h

8: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1 h, 2.) CHCl₃, Et₂O

9: 94 percent / tetrahydrofuran / 5 h / 70 °C

10: 76 percent / Bu₃SnH / toluene / 0.17 h / Heating

11: 96 percent / concd HCl / methanol / 2 h / 50 °C

12: Ph₃P, 1.0 M (EtOOCN)2, p-nitrobenzoic acid / diethyl ether / 17.5 h / Ambient temperature

13: 52.0 mg / 20percent (w/w) aq. NaOH / methanol / 2 h / 45 °C

14: Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

15: K₂CO₃ / CH₂Cl₂; methanol; tetrahydrofuran; H₂O / 1 h / 40 °C

16: 98 percent / DEPC, Et₃N / dimethylformamide / 0.5 h / 0 °C

17: 95 percent / H₂ / 20percent Pd(OH)2/C / dioxane / 1.5 h / 40 °C / 760 Torr

18: 94 percent / 4-dimethylaminopyridine, DCC / CH₂Cl₂ / 2 h / -20 °C

19: CH₂Cl₂ / 3 h / Ambient temperature

20: 10 percent / Bop-Cl, Et₃N / CH₂Cl₂ / 0 to 25 deg C, 6 h; 25 deg C, 13 h

With hydrogenchloride; dmap; lithium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; potassium carbonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; diethyl dicarbonate; diethylazodicarboxylate; 4-nitro-benzoic acid; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)81206-0

upstream raw materials:

4-methylpent-2-en-1-ol

(S)-4-methyl-pentane-1,3-diol

(S)-3-(benzyloxy)-4-methylpentanal

(S)-3-Benzyloxy-4-methyl-pentan-1-ol

Downstream raw materials:

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

(3R,9S,11S,13S,16S)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-16-isopropyl-4,9,11,13-tetramethyl-1-oxa-4,7-diaza-cyclohexadecane-2,5,8-trione

deiododoliculide silyl ether

deoxydoliculide silyl ether