(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

Base Information

• Chemical Name: (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
• CAS No.: 160531-34-0
• Molecular Formula: C₃₃H₅₅IN₂O₆Si
• Molecular Weight: 730.8
• Mol file: 160531-34-0.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 53 articles about (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 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: 89.0%

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) → (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 (160531-34-0)

Guidance literature:

With ammonium hydroxide; In methanol; for 1h; Ambient temperature;

DOI:10.1021/jo00096a003

Reference yield:

(2S,3R,5S)-5-Benzyloxy-3-methoxymethoxy-2,6-dimethyl-heptanal (160531-17-9) → (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 (160531-34-0)

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: 74 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

Reference yield:

(2S,3R,5S)-5-Benzyloxy-3-methoxymethoxy-2,6-dimethyl-heptanoic acid methoxy-methyl-amide (160531-39-5) → (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 (160531-34-0)

Guidance literature:

Multi-step reaction with 21 steps

1: 91 percent / 1.0 M DIBAL / tetrahydrofuran; hexane / 0.17 h / -78 °C

2: 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

3: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1.5 h, 2.) CHCl₃, Et₂O

4: 93 percent / tetrahydrofuran / 10 h / 70 °C

5: 79 percent / Bu₃SnH / toluene / 0.22 h / Heating

6: 97 percent / 1.0 M LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

7: 98 percent / DMSO, (COCl)2; Et₃N / CH₂Cl₂ / -78 °C / -78 deg C, 10 min; -78 to 0 deg C, 0 deg C, 10 min

8: 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

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

10: 94 percent / tetrahydrofuran / 5 h / 70 °C

11: 76 percent / Bu₃SnH / toluene / 0.17 h / Heating

12: 96 percent / concd HCl / methanol / 2 h / 50 °C

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

14: 52.0 mg / 20percent (w/w) aq. NaOH / methanol / 2 h / 45 °C

15: Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

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

17: 98 percent / DEPC, Et₃N / dimethylformamide / 0.5 h / 0 °C

18: 95 percent / H₂ / 20percent Pd(OH)2/C / dioxane / 1.5 h / 40 °C / 760 Torr

19: 94 percent / 4-dimethylaminopyridine, DCC / CH₂Cl₂ / 2 h / -20 °C

20: CH₂Cl₂ / 3 h / Ambient temperature

21: 74 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; diisobutylaluminium hydride; 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; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

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

upstream raw materials:

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

4-methylpent-2-en-1-ol

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

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

Downstream raw materials:

(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

deoxydoliculide silyl ether

Imidazole-1-carbothioic acid O-{(3R,9S,11S,13R,14S,16S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl} ester

deiododoliculide silyl ether