BOC-7-BROMO-L-TRYPTOPHAN

Base Information

• Chemical Name: BOC-7-BROMO-L-TRYPTOPHAN
• CAS No.: 612484-55-6
• Molecular Formula: C16H19BrN2O4
• Molecular Weight: 383.242
• Mol file: 612484-55-6.mol

Synonyms:Boc-7-Bromo-L-tryptophan;L-TRYPTOPHAN, 7-BROMO-N-[(1,1-DIMETHYLETHOXY)CARBONYL]-;

Chemical Property of BOC-7-BROMO-L-TRYPTOPHAN

Chemical Property:

• PSA: 91.42000
• LogP: 3.84170

Purity/Quality:

99%+, ^*data from raw suppliers

(S)-3-(7-Bromo-1H-indol-3-yl)-2-((tert-butoxycarbonyl)amino)propanoicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BOC-7-BROMO-L-TRYPTOPHAN

There total 5 articles about BOC-7-BROMO-L-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: 89.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-7-bromo-tryptophan (75816-19-2) → (S)-N-boc-7-bromo-tryptophan (612484-55-6)

Guidance literature:

In 1,4-dioxane; water; at 0 ℃;

DOI:10.1002/chem.201700680

Reference yield: 69.0%

di-tert-butyl dicarbonate (24424-99-5) + L-7-bromo-tryptophan trifluoroacetate → (S)-N-boc-7-bromo-tryptophan (612484-55-6)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water;

DOI:10.1002/chem.202002454 DOI:10.1002/chem.202103353

Reference yield:

7-bromo-1H-indole (51417-51-7) → (S)-N-boc-7-bromo-tryptophan (612484-55-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 9 percent / α2β2 tryptophane synthetase; HCl buffer; pyridoxal phosphate / toluene / 48 h / 37 °C

2: NaHCO₃ / dioxane; H₂O / 20 °C

With α2β2 tryptophane synthetase; HCl buffer; pyridoxal 5'-phosphate; sodium hydrogencarbonate; In 1,4-dioxane; water; toluene;

DOI:10.1021/ol035178f

upstream raw materials:

di-tert-butyl dicarbonate

(S)-7-bromo-tryptophan

7-bromo-1H-indole

tert-butyldicarbonate

Downstream raw materials:

C₂₃H₂₅BrIN₃O₄

2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-2-propylcarbamoyl-ethyl)-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester

2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-2-propylcarbamoyl-ethyl)-1H-indol-7-yl]-4-methoxy-phenyl}-propionic acid

C₅₆H₇₆BBrN₈O₁₂

Refernces

• 1、 Dachwitz, Steffen,Scharkowski, Bjarne,Sewald, Norbert. "Negishi Cross-Coupling Provides Alkylated Tryptophans and Tryptophan Regioisomers". supporting information. p. 18043 - 18046. Retrieved 2021/11/16.
• 2、 Foo, Klement,Newhouse, Timothy,Mori, Ikue,Takayama, Hiromitsu,Baran, Phil S.. "Total synthesis guided structure elucidation of (+)-psychotetramine". supporting information; experimental part. p. 2716 - 2719. Retrieved 2011/06/09.