N-[(1S,2R,3S)-2-bromo-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-1-[(S_S)-phenylsulfinylmethyl]butyl]-4-methyl-1-benzenesulfonamide

Base Information

• Chemical Name: N-[(1S,2R,3S)-2-bromo-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-1-[(S_S)-phenylsulfinylmethyl]butyl]-4-methyl-1-benzenesulfonamide
• CAS No.: 674777-54-9
• Molecular Formula: C₃₄H₄₀BrNO₅S₂Si
• Molecular Weight: 714.817

Synonyms:N-[(1S,2R,3S)-2-bromo-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-1-[(S_S)-phenylsulfinylmethyl]butyl]-4-methyl-1-benzenesulfonamide

Chemical Property of N-[(1S,2R,3S)-2-bromo-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-1-[(S_S)-phenylsulfinylmethyl]butyl]-4-methyl-1-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(1S,2R,3S)-2-bromo-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-1-[(S_S)-phenylsulfinylmethyl]butyl]-4-methyl-1-benzenesulfonamide

There total 9 articles about N-[(1S,2R,3S)-2-bromo-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-1-[(S_S)-phenylsulfinylmethyl]butyl]-4-methyl-1-benzenesulfonamide 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:

(E)-3-<(4R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl>-2-propen-1-ol (123751-18-8) → N-[(1S,2R,3S)-2-bromo-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-1-[(SS)-phenylsulfinylmethyl]butyl]-4-methyl-1-benzenesulfonamide (674777-54-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 83 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

2: 70 percent / methanol; camphor-10-sulfonic acid / 16 h / 20 °C

3: 63 percent / PBu₃ / tetrahydrofuran / 36 h / 72 °C

4: 45 percent / NaIO₄ / methanol; H₂O / 16.5 h / 0 - 20 °C

5: CH₂Cl₂ / 0.5 h / 0 °C

6: triethylamine / CH₂Cl₂ / 0 - 20 °C

7: aq. NaOH / methanol / 0 - 20 °C

8: imidazole / CH₂Cl₂ / 20 °C

9: 51 percent / N-bromosuccinimide; water / toluene / 20 °C

With 1H-imidazole; methanol; sodium hydroxide; sodium periodate; N-Bromosuccinimide; tributylphosphine; camphor-10-sulfonic acid; water; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; toluene;

DOI:10.1016/j.tetasy.2003.11.036

Reference yield:

(4R)-4-(2-ethoxycarbonyl-vinyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (131713-27-4,134525-18-1,144070-31-5,149406-02-0) → N-[(1S,2R,3S)-2-bromo-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-1-[(SS)-phenylsulfinylmethyl]butyl]-4-methyl-1-benzenesulfonamide (674777-54-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 73 percent / diisobutylaluminium hydride; n-BuLi / toluene; hexane / 1.33 h / -78 - 20 °C

2: 83 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

3: 70 percent / methanol; camphor-10-sulfonic acid / 16 h / 20 °C

4: 63 percent / PBu₃ / tetrahydrofuran / 36 h / 72 °C

5: 45 percent / NaIO₄ / methanol; H₂O / 16.5 h / 0 - 20 °C

6: CH₂Cl₂ / 0.5 h / 0 °C

7: triethylamine / CH₂Cl₂ / 0 - 20 °C

8: aq. NaOH / methanol / 0 - 20 °C

9: imidazole / CH₂Cl₂ / 20 °C

10: 51 percent / N-bromosuccinimide; water / toluene / 20 °C

With 1H-imidazole; methanol; sodium hydroxide; sodium periodate; N-Bromosuccinimide; n-butyllithium; tributylphosphine; camphor-10-sulfonic acid; water; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene;

DOI:10.1016/j.tetasy.2003.11.036

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → N-[(1S,2R,3S)-2-bromo-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-1-[(SS)-phenylsulfinylmethyl]butyl]-4-methyl-1-benzenesulfonamide (674777-54-9)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / CH₂Cl₂ / 0 - 20 °C

2: aq. NaOH / methanol / 0 - 20 °C

3: imidazole / CH₂Cl₂ / 20 °C

4: 51 percent / N-bromosuccinimide; water / toluene / 20 °C

With 1H-imidazole; sodium hydroxide; N-Bromosuccinimide; water; triethylamine; In methanol; dichloromethane; toluene;

DOI:10.1016/j.tetasy.2003.11.036

upstream raw materials:

(E)-3-<(4R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl>-2-propen-1-ol

(4R)-4-(2-ethoxycarbonyl-vinyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

p-toluenesulfonyl chloride

(2E,4R)-4-(tert-butyloxycarbonylamino)-5-hydroxy-2-pentenyl pivalate

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