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

Base Information

• Chemical Name: (2S,5S,6S)-5-azido-6-benzyloxy-2-[(tert-butoxycarbonyl)amino]-1,8-[(methylsulfonyl)oxy]octane
• CAS No.: 457614-07-2
• Molecular Formula: C₂₂H₃₆N₄O₉S₂
• Molecular Weight: 564.681
• Mol file: 457614-07-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (2S,5S,6S)-5-azido-6-benzyloxy-2-[(tert-butoxycarbonyl)amino]-1,8-[(methylsulfonyl)oxy]octane 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:

2,2-dimethyl-3-<(1,1-dimethylethoxy)carbonyl>-4(S)-oxazolidinepropanal (144090-56-2) → (2S,5S,6S)-5-azido-6-benzyloxy-2-[(tert-butoxycarbonyl)amino]-1,8-[(methylsulfonyl)oxy]octane (457614-07-2)

Guidance literature:

Multi-step reaction with 10 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

6.1: 95 mg / aq. CAN / acetonitrile / 0.17 h / 0 °C

7.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

7.2: 90 percent / tetrahydrofuran / 48 h / 20 °C

8.1: TBAF / tetrahydrofuran / 4 h / 20 °C

9.1: 295 mg / aq. AcOH / tetrahydrofuran / 12 h / 55 - 60 °C

10.1: DMAP; pyridine / 2 h / 0 °C

With pyridine; 1H-imidazole; dmap; ammonium cerium(IV) nitrate; di-isopropyl azodicarboxylate; diphenyl-phosphinic acid; borane; tetrabutyl ammonium fluoride; sec.-butyllithium; sodium hydride; acetic acid; triphenylphosphine; In tetrahydrofuran; dichloromethane; cyclohexane; acetonitrile;

DOI:10.1055/s-2002-28505

Reference yield:

(3R,4S)-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-4-(4-methoxyphenoxy)hex-5-en-3-ol (457613-95-5) → (2S,5S,6S)-5-azido-6-benzyloxy-2-[(tert-butoxycarbonyl)amino]-1,8-[(methylsulfonyl)oxy]octane (457614-07-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 87 percent / imidazole / CH₂Cl₂ / 20 °C

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

2.2: aq. H₂O₂; NaOH / 2 h / 20 °C

2.3: 1.56 g / TBAF / tetrahydrofuran / 20 °C

3.1: 94 percent / imidazole / CH₂Cl₂ / 20 °C

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

5.1: 95 mg / aq. CAN / acetonitrile / 0.17 h / 0 °C

6.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

6.2: 90 percent / tetrahydrofuran / 48 h / 20 °C

7.1: TBAF / tetrahydrofuran / 4 h / 20 °C

8.1: 295 mg / aq. AcOH / tetrahydrofuran / 12 h / 55 - 60 °C

9.1: DMAP; pyridine / 2 h / 0 °C

With pyridine; 1H-imidazole; dmap; ammonium cerium(IV) nitrate; di-isopropyl azodicarboxylate; diphenyl-phosphinic acid; borane; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; triphenylphosphine; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1055/s-2002-28505

Reference yield:

(3S,4R)-6-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-3-(4-methoxyphenoxy)hexan-1,4-diol (457613-98-8) → (2S,5S,6S)-5-azido-6-benzyloxy-2-[(tert-butoxycarbonyl)amino]-1,8-[(methylsulfonyl)oxy]octane (457614-07-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 94 percent / imidazole / CH₂Cl₂ / 20 °C

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

3.1: 95 mg / aq. CAN / acetonitrile / 0.17 h / 0 °C

4.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

4.2: 90 percent / tetrahydrofuran / 48 h / 20 °C

5.1: TBAF / tetrahydrofuran / 4 h / 20 °C

6.1: 295 mg / aq. AcOH / tetrahydrofuran / 12 h / 55 - 60 °C

7.1: DMAP; pyridine / 2 h / 0 °C

With pyridine; 1H-imidazole; dmap; ammonium cerium(IV) nitrate; di-isopropyl azodicarboxylate; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; triphenylphosphine; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1055/s-2002-28505

upstream raw materials:

methanesulfonyl chloride

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

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

(3R,4S)-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-4-(4-methoxyphenoxy)hex-5-en-3-ol

Downstream raw materials:

((1S,6S,8aS)-1-Hydroxy-octahydro-indolizin-6-yl)-carbamic acid tert-butyl ester

(1S,6S,8aS)-1-acetoxy-6-aminooctahydroindolizidine

(1S,6S,8aS)-6-[(tert-butoxycarbonyl)amino]-1-benzyloxyoctahydroindolizidine