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

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Chemical Name:(3S,4S)-3-azido-4-benzyloxy-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-6-[(tert-butyldiphenylsilyl)oxy]hexane
CAS No.:457614-02-7
Molecular Formula:C₃₉H₅₄N₄O₅Si
Molecular Weight:686.967
Hs Code.:

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

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

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

There total 8 articles about (3S,4S)-3-azido-4-benzyloxy-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-6-[(tert-butyldiphenylsilyl)oxy]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: 90.0%

: 100-39-0
benzyl bromide

: 457614-01-6
(3S,4S)-4-azido-6-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-1-[(tert-butyldiphenylsilyl)oxy]hexan-3-ol

: 457614-02-7
(3S,4S)-3-azido-4-benzyloxy-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-6-[(tert-butyldiphenylsilyl)oxy]hexane

Guidance literature:: (3S,4S)-4-azido-6-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-1-[(tert-butyldiphenylsilyl)oxy]hexan-3-ol; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.166667h;

benzyl bromide; In tetrahydrofuran; at 20 ℃; for 48h;
DOI:10.1055/s-2002-28505

Reference yield:

: 144090-56-2
2,2-dimethyl-3-<(1,1-dimethylethoxy)carbonyl>-4(S)-oxazolidinepropanal

: 457614-02-7
(3S,4S)-3-azido-4-benzyloxy-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-6-[(tert-butyldiphenylsilyl)oxy]hexane

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; ammonium cerium(IV) nitrate; di-isopropyl azodicarboxylate; diphenyl-phosphinic acid; borane; sec.-butyllithium; sodium hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane; cyclohexane; acetonitrile;
DOI:10.1055/s-2002-28505

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 457614-02-7
(3S,4S)-3-azido-4-benzyloxy-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-6-[(tert-butyldiphenylsilyl)oxy]hexane

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; ammonium cerium(IV) nitrate; di-isopropyl azodicarboxylate; diphenyl-phosphinic acid; sodium hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1055/s-2002-28505