(R)-4-bromo-1-(tert-butyloxycarbonyl)-α-N-(9-phenyl-9-fluorenyl)tryptophan

Base Information

Chemical Name:(R)-4-bromo-1-(tert-butyloxycarbonyl)-α-N-(9-phenyl-9-fluorenyl)tryptophan
CAS No.:219943-49-4
Molecular Formula:C₃₅H₃₁BrN₂O₄
Molecular Weight:623.546
Hs Code.:

Synonyms:(R)-4-bromo-1-(tert-butyloxycarbonyl)-α-N-(9-phenyl-9-fluorenyl)tryptophan

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Chemical Property of (R)-4-bromo-1-(tert-butyloxycarbonyl)-α-N-(9-phenyl-9-fluorenyl)tryptophan

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Technology Process of (R)-4-bromo-1-(tert-butyloxycarbonyl)-α-N-(9-phenyl-9-fluorenyl)tryptophan

There total 12 articles about (R)-4-bromo-1-(tert-butyloxycarbonyl)-α-N-(9-phenyl-9-fluorenyl)tryptophan 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: 69.0%

: 219943-47-2
4-Bromo-3-[(R)-3-oxo-2-(9-phenyl-9H-fluoren-9-ylamino)-propyl]-indole-1-carboxylic acid tert-butyl ester

: 219943-49-4
(R)-4-bromo-1-(tert-butyloxycarbonyl)-α-N-(9-phenyl-9-fluorenyl)tryptophan

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; acetonitrile; tert-butyl alcohol; at 0 ℃; for 0.166667h;
DOI:10.1021/jo981723s

Reference yield:

: 52488-36-5
4-bromo-1H-indole

: 219943-49-4
(R)-4-bromo-1-(tert-butyloxycarbonyl)-α-N-(9-phenyl-9-fluorenyl)tryptophan

Guidance literature:: Multi-step reaction with 9 steps

1: 31.0 g / pyridinium bromide perbromide / pyridine / 0.25 h / 0 °C

2: Et₃N, DMAP / tetrahydrofuran / 14 h

3: 1.) n-BuLi / 1.) THF, -78 deg C, 90 min, 2.) THF, -75 deg C, 4 h

4: 99 percent / NaOMe / tetrahydrofuran / 1 h / Ambient temperature

5: 91 percent / DMAO, BH₃*THF / tetrahydrofuran / 72 h / 0 °C

6: 95 percent / DMAP / tetrahydrofuran / 4 h / Ambient temperature

7: 86 percent / 1M HCl / ethyl acetate / 1.) 0 deg C to room temperature, 1 h, 2.) room temperature, 4 h

8: 1.) NCS, DMS, 2.) Et₃N / 1.) toluene, -25 deg C, 6 h, 2.) -25 deg C, 10 min; room temperature, 1 h

9: 69 percent / 2-methyl-2-butene, NaClO₂, NaH₂PO₄ / acetonitrile; 2-methyl-propan-2-ol; H₂O / 0.17 h / 0 °C

With hydrogenchloride; dmap; sodium chlorite; sodium dihydrogenphosphate; N-chloro-succinimide; n-butyllithium; borane-THF; 2-methyl-but-2-ene; 2,3-dimercapto-succinic acid; sodium methylate; pyridinium hydrobromide perbromide; triethylamine; In tetrahydrofuran; pyridine; water; ethyl acetate; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo981723s

Reference yield:

: 122213-51-8
N-(9-phenylfluoren-9-yl)-L-serine isoxazolidide

: 219943-49-4
(R)-4-bromo-1-(tert-butyloxycarbonyl)-α-N-(9-phenyl-9-fluorenyl)tryptophan

Guidance literature:: Multi-step reaction with 9 steps

1: 99 percent / DIEA / CH₂Cl₂ / 20 h / Ambient temperature

2: 96 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C

3: 1.) n-BuLi / 1.) THF, -78 deg C, 90 min, 2.) THF, -75 deg C, 4 h

4: 99 percent / NaOMe / tetrahydrofuran / 1 h / Ambient temperature

5: 91 percent / DMAO, BH₃*THF / tetrahydrofuran / 72 h / 0 °C

6: 95 percent / DMAP / tetrahydrofuran / 4 h / Ambient temperature

7: 86 percent / 1M HCl / ethyl acetate / 1.) 0 deg C to room temperature, 1 h, 2.) room temperature, 4 h

8: 1.) NCS, DMS, 2.) Et₃N / 1.) toluene, -25 deg C, 6 h, 2.) -25 deg C, 10 min; room temperature, 1 h

9: 69 percent / 2-methyl-2-butene, NaClO₂, NaH₂PO₄ / acetonitrile; 2-methyl-propan-2-ol; H₂O / 0.17 h / 0 °C

With hydrogenchloride; dmap; sodium chlorite; sodium dihydrogenphosphate; N-chloro-succinimide; lithium aluminium tetrahydride; n-butyllithium; borane-THF; 2-methyl-but-2-ene; 2,3-dimercapto-succinic acid; sodium methylate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo981723s