BOC-5-FLUORO-D-TRYPTOPHAN

Base Information

• Chemical Name: BOC-5-FLUORO-D-TRYPTOPHAN
• CAS No.: 114926-41-9
• Molecular Formula: C16H19FN2O4
• Molecular Weight: 322.33100
• Hs Code.: 2933998090
• Mol file: 114926-41-9.mol

Synonyms:Boc-5-Fluoro-D-tryptophan;

Chemical Property of BOC-5-FLUORO-D-TRYPTOPHAN

Chemical Property:

• Boiling Point: 538.3±50.0 °C(Predicted)
• PKA: 3.82±0.10(Predicted)
• PSA: 94.91000
• Density: 1.314±0.06 g/cm3(Predicted)
• LogP: 3.03180

Purity/Quality:

99%+, ^*data from raw suppliers

(2R)-2-(Tert-Butoxycarbonylamino)-3-(5-Fluoro-1H-Indol-3-Yl)Propanoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BOC-5-FLUORO-D-TRYPTOPHAN

There total 9 articles about BOC-5-FLUORO-D-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: 93.0%

(3S,5S,6R)-tert-butyl 3-((5-fluoro-1H-indol-3-yl)methyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate → (S)-2-((tert-butoxycarbonyl)amino)-3-(5-fluoro-1H-indol-3-yl)propanoic acid (114926-41-9,53478-53-8)

Guidance literature:

With trimethylsilyl iodide; In dichloromethane; for 0.333333h;

DOI:10.1016/j.tetlet.2015.09.017

Reference yield: 92.0%

di-tert-butyl dicarbonate (24424-99-5) + DL-5-fluorotryptophan (154-08-5,343-91-9,97749-24-1) → 2-((tert-butoxycarbonyl)amino)-3-(5-fluoro-1H-indol-3-yl)propanoic acid (67337-05-7,114926-41-9,53478-53-8)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1021/acs.jmedchem.8b02027

Reference yield: 92.0%

→ 2-((tert-butoxycarbonyl)amino)-3-(5-fluoro-1H-indol-3-yl)propanoic acid (67337-05-7,114926-41-9,53478-53-8)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; at 20 ℃;

upstream raw materials:

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

DL-5-fluorotryptophan

di-tert-butyl dicarbonate

3-dimethylaminomethyl-5-fluoroindole

Downstream raw materials:

5-fluoro-L-tryptophan

t-butoxycarbonyl-DL-6-fluorotryptophan

Refernces

• 1、 -. "PCSK9 ANTAGONIST COMPOUNDS". Page/Page column 51; 53. . Retrieved 2021/06/26.
• 2、 Jiang, Min,Peng, Lei,Yang, Kai,Wang, Tianqi,Yan, Xueming,Jiang, Tao,Xu, Jianrong,Qi, Jin,Zhou, Hanbing,Qian, Niandong,Zhou, Qi,Chen, Bo,Xu, Xing,Deng, Lianfu,Yang, Chunhao. "Development of Small-Molecules Targeting Receptor Activator of Nuclear Factor-κB Ligand (RANKL) - Receptor Activator of Nuclear Factor-κB (RANK) Protein-Protein Interaction by Structure-Based Virtual Screening and Hit Optimization". supporting information. p. 5370 - 5381. Retrieved 2019/06/24.