[5-(tert-Butyl-dimethyl-silanyloxy)-6-((2E,4E,10E)-(6S,7S,8R,9S)-7,9-dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoylamino)-6-trimethylsilanyl-hexanoylamino]-acetic acid methyl ester

Base Information

• Chemical Name: [5-(tert-Butyl-dimethyl-silanyloxy)-6-((2E,4E,10E)-(6S,7S,8R,9S)-7,9-dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoylamino)-6-trimethylsilanyl-hexanoylamino]-acetic acid methyl ester
• CAS No.: 443123-86-2
• Molecular Formula: C₄₀H₆₈N₂O₇Si₂
• Molecular Weight: 745.16
• Mol file: 443123-86-2.mol

Synonyms:[5-(tert-Butyl-dimethyl-silanyloxy)-6-((2E,4E,10E)-(6S,7S,8R,9S)-7,9-dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoylamino)-6-trimethylsilanyl-hexanoylamino]-acetic acid methyl ester

Chemical Property of [5-(tert-Butyl-dimethyl-silanyloxy)-6-((2E,4E,10E)-(6S,7S,8R,9S)-7,9-dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoylamino)-6-trimethylsilanyl-hexanoylamino]-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [5-(tert-Butyl-dimethyl-silanyloxy)-6-((2E,4E,10E)-(6S,7S,8R,9S)-7,9-dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoylamino)-6-trimethylsilanyl-hexanoylamino]-acetic acid methyl ester

There total 15 articles about [5-(tert-Butyl-dimethyl-silanyloxy)-6-((2E,4E,10E)-(6S,7S,8R,9S)-7,9-dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoylamino)-6-trimethylsilanyl-hexanoylamino]-acetic acid methyl 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:

5-tert-butyldimethylsilyloxypentanal (87184-80-3) → [5-(tert-Butyl-dimethyl-silanyloxy)-6-((2E,4E,10E)-(6S,7S,8R,9S)-7,9-dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoylamino)-6-trimethylsilanyl-hexanoylamino]-acetic acid methyl ester (443123-86-2)

Guidance literature:

Multi-step reaction with 14 steps

1: PPh₃; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: nBuLi / tetrahydrofuran / 0.5 h / -78 °C

3: camphorsulfonic acid / methanol; CH₂Cl₂ / 0.5 h / 0 °C

4: H₂ / Lindlar's catalyst / hexane

5: 79 percent / mCPBA / CH₂Cl₂ / 0.75 h / 0 - 20 °C

6: 88 percent / NaN₃; NH₄Cl / methanol; H₂O / 15 h / 0 - 20 °C

7: LiAlH₄ / diethyl ether / 2 h / 0 - 20 °C

8: EDCI; HOBt / CH₂Cl₂ / 5.25 h / 0 - 20 °C

9: 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

10: camphorsulfonic acid / methanol; CH₂Cl₂ / 5 h / 0 °C

11: SO₃-py; Et₃N; DMSO / CH₂Cl₂ / 0.5 h / 0 °C

12: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C

13: N-methylmorpholine / CH₂Cl₂ / 0.25 h / 0 °C

14: DIPEA / dimethylformamide / 4 h / 0 - 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; sodium azide; 2-methyl-but-2-ene; pyridine-SO₃ complex; camphor-10-sulfonic acid; hydrogen; ammonium chloride; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/S0040-4039(02)00289-7

Reference yield:

6-trimethylsilanyl-hex-5-yn-1-ol (103437-52-1) → [5-(tert-Butyl-dimethyl-silanyloxy)-6-((2E,4E,10E)-(6S,7S,8R,9S)-7,9-dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoylamino)-6-trimethylsilanyl-hexanoylamino]-acetic acid methyl ester (443123-86-2)

Guidance literature:

Multi-step reaction with 11 steps

1: H₂ / Lindlar's catalyst / hexane

2: 79 percent / mCPBA / CH₂Cl₂ / 0.75 h / 0 - 20 °C

3: 88 percent / NaN₃; NH₄Cl / methanol; H₂O / 15 h / 0 - 20 °C

4: LiAlH₄ / diethyl ether / 2 h / 0 - 20 °C

5: EDCI; HOBt / CH₂Cl₂ / 5.25 h / 0 - 20 °C

6: 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

7: camphorsulfonic acid / methanol; CH₂Cl₂ / 5 h / 0 °C

8: SO₃-py; Et₃N; DMSO / CH₂Cl₂ / 0.5 h / 0 °C

9: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C

10: N-methylmorpholine / CH₂Cl₂ / 0.25 h / 0 °C

11: DIPEA / dimethylformamide / 4 h / 0 - 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; sodium azide; 2-methyl-but-2-ene; pyridine-SO₃ complex; camphor-10-sulfonic acid; hydrogen; ammonium chloride; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; In methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/S0040-4039(02)00289-7

Reference yield:

5-(tert-butyldimethyl-silyloxy)pentan-1-ol (83067-20-3) → [5-(tert-Butyl-dimethyl-silanyloxy)-6-((2E,4E,10E)-(6S,7S,8R,9S)-7,9-dimethoxy-3,6,8-trimethyl-11-phenyl-undeca-2,4,10-trienoylamino)-6-trimethylsilanyl-hexanoylamino]-acetic acid methyl ester (443123-86-2)

Guidance literature:

Multi-step reaction with 15 steps

1: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 °C

2: PPh₃; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: nBuLi / tetrahydrofuran / 0.5 h / -78 °C

4: camphorsulfonic acid / methanol; CH₂Cl₂ / 0.5 h / 0 °C

5: H₂ / Lindlar's catalyst / hexane

6: 79 percent / mCPBA / CH₂Cl₂ / 0.75 h / 0 - 20 °C

7: 88 percent / NaN₃; NH₄Cl / methanol; H₂O / 15 h / 0 - 20 °C

8: LiAlH₄ / diethyl ether / 2 h / 0 - 20 °C

9: EDCI; HOBt / CH₂Cl₂ / 5.25 h / 0 - 20 °C

10: 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

11: camphorsulfonic acid / methanol; CH₂Cl₂ / 5 h / 0 °C

12: SO₃-py; Et₃N; DMSO / CH₂Cl₂ / 0.5 h / 0 °C

13: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C

14: N-methylmorpholine / CH₂Cl₂ / 0.25 h / 0 °C

15: DIPEA / dimethylformamide / 4 h / 0 - 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; sodium azide; 2-methyl-but-2-ene; oxalyl dichloride; pyridine-SO₃ complex; camphor-10-sulfonic acid; hydrogen; ammonium chloride; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Swern oxidation;

DOI:10.1016/S0040-4039(02)00289-7

upstream raw materials:

glycine ethyl ester hydrochloride

5-(tert-butyldimethyl-silyloxy)pentan-1-ol

5-tert-butyldimethylsilyloxypentanal

6-trimethylsilanyl-hex-5-yn-1-ol