(3S,4S)-3-azido-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-6-[(tert-butyldiphenylsilyl)oxy]-4-(4-methoxyphenoxy)hexane

Base Information

• Chemical Name: (3S,4S)-3-azido-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-6-[(tert-butyldiphenylsilyl)oxy]-4-(4-methoxyphenoxy)hexane
• CAS No.: 457614-00-5
• Molecular Formula: C₃₉H₅₄N₄O₆Si
• Molecular Weight: 702.966
• Mol file: 457614-00-5.mol

Synonyms:

Chemical Property of (3S,4S)-3-azido-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-6-[(tert-butyldiphenylsilyl)oxy]-4-(4-methoxyphenoxy)hexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3-azido-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-6-[(tert-butyldiphenylsilyl)oxy]-4-(4-methoxyphenoxy)hexane

There total 7 articles about (3S,4S)-3-azido-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-6-[(tert-butyldiphenylsilyl)oxy]-4-(4-methoxyphenoxy)hexane 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:

(3R,4S)-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-6-[(tert-butyldiphenylsilyl)oxy]-4-(4-methoxyphenoxy)hexan-3-ol (457613-99-9) → (3S,4S)-3-azido-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-6-[(tert-butyldiphenylsilyl)oxy]-4-(4-methoxyphenoxy)hexane (457614-00-5)

Guidance literature:

With di-isopropyl azodicarboxylate; diphenyl-phosphinic acid; triphenylphosphine; at 0 - 20 ℃; for 12h;

DOI:10.1055/s-2002-28505

Reference yield:

allyl (4-methoxyphenyl) ether (13391-35-0) → (3S,4S)-3-azido-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-6-[(tert-butyldiphenylsilyl)oxy]-4-(4-methoxyphenoxy)hexane (457614-00-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sec-BuLi / tetrahydrofuran; cyclohexane / 0.42 h / -78 °C

1.2: chiral cyclopentadienyl titanium complex / tetrahydrofuran; cyclohexane; diethyl ether / 3 h / -78 °C

1.3: 69 percent / tetrahydrofuran; cyclohexane; diethyl ether / 4 h / -78 °C

2.1: 87 percent / imidazole / CH₂Cl₂ / 20 °C

3.1: BH₃ / tetrahydrofuran / 4 h / 0 - 20 °C

3.2: aq. H₂O₂; NaOH / 2 h / 20 °C

3.3: 1.56 g / TBAF / tetrahydrofuran / 20 °C

4.1: 94 percent / imidazole / CH₂Cl₂ / 20 °C

5.1: DPPA; PPh₃; DIAD / 12 h / 0 - 20 °C

With 1H-imidazole; di-isopropyl azodicarboxylate; diphenyl-phosphinic acid; borane; sec.-butyllithium; triphenylphosphine; In tetrahydrofuran; dichloromethane; cyclohexane;

DOI:10.1055/s-2002-28505

Reference yield:

2,2-dimethyl-3-<(1,1-dimethylethoxy)carbonyl>-4(S)-oxazolidinepropanal (144090-56-2) → (3S,4S)-3-azido-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-6-[(tert-butyldiphenylsilyl)oxy]-4-(4-methoxyphenoxy)hexane (457614-00-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sec-BuLi / tetrahydrofuran; cyclohexane / 0.42 h / -78 °C

1.2: chiral cyclopentadienyl titanium complex / tetrahydrofuran; cyclohexane; diethyl ether / 3 h / -78 °C

1.3: 69 percent / tetrahydrofuran; cyclohexane; diethyl ether / 4 h / -78 °C

2.1: 87 percent / imidazole / CH₂Cl₂ / 20 °C

3.1: BH₃ / tetrahydrofuran / 4 h / 0 - 20 °C

3.2: aq. H₂O₂; NaOH / 2 h / 20 °C

3.3: 1.56 g / TBAF / tetrahydrofuran / 20 °C

4.1: 94 percent / imidazole / CH₂Cl₂ / 20 °C

5.1: DPPA; PPh₃; DIAD / 12 h / 0 - 20 °C

With 1H-imidazole; di-isopropyl azodicarboxylate; diphenyl-phosphinic acid; borane; sec.-butyllithium; triphenylphosphine; In tetrahydrofuran; dichloromethane; cyclohexane;

DOI:10.1055/s-2002-28505

upstream raw materials:

(3R,4S)-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-6-[(tert-butyldiphenylsilyl)oxy]-4-(4-methoxyphenoxy)hexan-3-ol

allyl (4-methoxyphenyl) ether

2,2-dimethyl-3-<(1,1-dimethylethoxy)carbonyl>-4(S)-oxazolidinepropanal

tert-butylchlorodiphenylsilane

Downstream raw materials:

(3S,4S)-4-azido-6-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-1-[(tert-butyldiphenylsilyl)oxy]hexan-3-ol

(3S,4S)-3-azido-4-benzyloxy-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-6-[(tert-butyldiphenylsilyl)oxy]hexane

(2S,5S,6S)-5-azido-6-benzyloxy-2-[(tert-butoxycarbonyl)amino]-1,8-[(methylsulfonyl)oxy]octane

(2S,5S,6S)-5-azido-6-benzyloxy-2-[(tert-butoxycarbonyl)amino]octan-1,8-diol