(3S,9S,11S,13R,14S,16S)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-14-hydroxy-16-isopropyl-4,9,11,13-tetramethyl-1-oxa-4,7-diaza-cyclohexadecane-2,5,8-trione

Base Information

• Chemical Name: (3S,9S,11S,13R,14S,16S)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-14-hydroxy-16-isopropyl-4,9,11,13-tetramethyl-1-oxa-4,7-diaza-cyclohexadecane-2,5,8-trione
• CAS No.: 162061-68-9
• Molecular Formula: C₃₃H₅₅IN₂O₆Si
• Molecular Weight: 730.8
• Mol file: 162061-68-9.mol

Synonyms:

Chemical Property of (3S,9S,11S,13R,14S,16S)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-14-hydroxy-16-isopropyl-4,9,11,13-tetramethyl-1-oxa-4,7-diaza-cyclohexadecane-2,5,8-trione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,9S,11S,13R,14S,16S)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-14-hydroxy-16-isopropyl-4,9,11,13-tetramethyl-1-oxa-4,7-diaza-cyclohexadecane-2,5,8-trione

There total 22 articles about (3S,9S,11S,13R,14S,16S)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-14-hydroxy-16-isopropyl-4,9,11,13-tetramethyl-1-oxa-4,7-diaza-cyclohexadecane-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:

(2S,4R,5R,7S)-7-Benzyloxy-5-methoxymethoxy-2,4,8-trimethyl-nonanoic acid methyl ester (160531-20-4) → (3S,9S,11S,13R,14S,16S)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-14-hydroxy-16-isopropyl-4,9,11,13-tetramethyl-1-oxa-4,7-diaza-cyclohexadecane-2,5,8-trione (162061-68-9)

Guidance literature:

Multi-step reaction with 16 steps

1: 97 percent / 1.0 M LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

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

3: 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

4: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1 h, 2.) CHCl₃, Et₂O

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

6: 76 percent / Bu₃SnH / toluene / 0.17 h / Heating

7: 96 percent / concd HCl / methanol / 2 h / 50 °C

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

9: 52.0 mg / 20percent (w/w) aq. NaOH / methanol / 2 h / 45 °C

10: Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

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

12: 98 percent / DEPC, Et₃N / dimethylformamide / 0.5 h / 0 °C

13: 95 percent / H₂ / 20percent Pd(OH)2/C / dioxane / 1.5 h / 40 °C / 760 Torr

14: 97 percent / 4-dimethylaminopyridine, DCC / CH₂Cl₂ / 2 h / -20 °C

15: CH₂Cl₂ / 3 h / Ambient temperature

16: Bop-Cl, Et₃N / CH₂Cl₂ / 0 to 15 deg C, 12 h; 25 deg C, 1 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,4S,6R,7S,9S)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,10-tetramethyl-undecanoic acid (162061-66-7) → (3S,9S,11S,13R,14S,16S)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-14-hydroxy-16-isopropyl-4,9,11,13-tetramethyl-1-oxa-4,7-diaza-cyclohexadecane-2,5,8-trione (162061-68-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / DEPC, Et₃N / dimethylformamide / 0.5 h / 0 °C

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

3: 97 percent / 4-dimethylaminopyridine, DCC / CH₂Cl₂ / 2 h / -20 °C

4: CH₂Cl₂ / 3 h / Ambient temperature

5: Bop-Cl, Et₃N / CH₂Cl₂ / 0 to 15 deg C, 12 h; 25 deg C, 1 h

With dmap; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; dicyclohexyl-carbodiimide; diethyl dicarbonate; palladium dihydroxide; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

(2S,3R,4S,6R,7R,9S)-9-Benzyloxy-3-hydroxy-7-methoxymethoxy-2,4,6,10-tetramethyl-undecanoic acid methyl ester (160531-43-1) → (3S,9S,11S,13R,14S,16S)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-14-hydroxy-16-isopropyl-4,9,11,13-tetramethyl-1-oxa-4,7-diaza-cyclohexadecane-2,5,8-trione (162061-68-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 94 percent / tetrahydrofuran / 5 h / 70 °C

2: 76 percent / Bu₃SnH / toluene / 0.17 h / Heating

3: 96 percent / concd HCl / methanol / 2 h / 50 °C

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

5: 52.0 mg / 20percent (w/w) aq. NaOH / methanol / 2 h / 45 °C

6: Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

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

8: 98 percent / DEPC, Et₃N / dimethylformamide / 0.5 h / 0 °C

9: 95 percent / H₂ / 20percent Pd(OH)2/C / dioxane / 1.5 h / 40 °C / 760 Torr

10: 97 percent / 4-dimethylaminopyridine, DCC / CH₂Cl₂ / 2 h / -20 °C

11: CH₂Cl₂ / 3 h / Ambient temperature

12: Bop-Cl, Et₃N / CH₂Cl₂ / 0 to 15 deg C, 12 h; 25 deg C, 1 h

With hydrogenchloride; dmap; sodium hydroxide; hydrogen; tri-n-butyl-tin hydride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; potassium carbonate; 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:

(2S,3R,5S)-5-Benzyloxy-3-methoxymethoxy-2,6-dimethyl-heptanal

(2S,4R,5R,7S)-7-Benzyloxy-5-methoxymethoxy-2,4,8-trimethyl-nonan-1-ol

(2S,4R,5R,7S)-7-Benzyloxy-5-methoxymethoxy-2,4,8-trimethyl-nonanal

(2S,4R,5R,7S)-7-Benzyloxy-5-methoxymethoxy-2,4,8-trimethyl-nonanoic acid methyl ester