BOC-5-HYDROXY-L-TRYPTOPHAN

Base Information

• Chemical Name: BOC-5-HYDROXY-L-TRYPTOPHAN
• CAS No.: 119768-45-5
• Molecular Formula: C16H20N2O5
• Molecular Weight: 320.34000
• Hs Code.: 2933990090
• Mol file: 119768-45-5.mol

Synonyms:BOC-2-AMINO-3-(5-HYDROXYINDOLYL)PROPIONIC ACID;Boc-5HTP-OH;(S)-2-tert-butoxy-carbonylamino-3-(5-hydroxy-1H-indol-3-yl)-propionic acid;BOC-L-5-HYDROXYTRYPTOPHAN;BOC-TRP(5-OH)-OH;

Chemical Property of BOC-5-HYDROXY-L-TRYPTOPHAN

Chemical Property:

• PSA: 111.65000
• LogP: 2.78480

Purity/Quality:

98%min ^*data from raw suppliers

Boc-5-hydroxy-L-tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Boc-5-hydroxy-L-tryptophan is a related compound of the amino acid L-Tryptophan (CAT# T947210). It can be used in the synthesis of tryptophan-derived butyrylcholinesterase inhibitors as anti-Alzheimer''s agents. It can also be useful in the design of compounds recognized by the L-type amino acid transporter 1.

Technology Process of BOC-5-HYDROXY-L-TRYPTOPHAN

There total 4 articles about BOC-5-HYDROXY-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: 76.0%

di-tert-butyl dicarbonate (24424-99-5) + L-5-HTP (4350-09-8,4298-20-8) → (S)-2-((tert-butoxycarbonyl)amino)-3-(5-hydroxy-1H-indol-3-yl)propanoic acid (119768-45-5,185525-63-7)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; water; at 20 ℃; for 2h;

Reference yield: 72.0%

(3S,5S,6R)-tert-butyl 3-((5-(benzyloxy)-1H-indol-3-yl)methyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate → (S)-2-((tert-butoxycarbonyl)amino)-3-(5-hydroxy-1H-indol-3-yl)propanoic acid (119768-45-5,185525-63-7)

Guidance literature:

With ammonia; lithium; tert-butyl alcohol; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2015.09.017

Reference yield:

5-benzyloxygramine (1453-97-0) → (S)-2-((tert-butoxycarbonyl)amino)-3-(5-hydroxy-1H-indol-3-yl)propanoic acid (119768-45-5,185525-63-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic acid / tetrahydrofuran / 1 h / 0 °C

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

2.2: 1.5 h / -78 °C

3.1: lithium; ammonia; tert-butyl alcohol / tetrahydrofuran / 0.5 h / -78 °C

With ammonia; lithium; acetic acid; lithium hexamethyldisilazane; tert-butyl alcohol; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2015.09.017

upstream raw materials:

di-tert-butyl dicarbonate

L-5-HTP

5-benzyloxygramine

Downstream raw materials:

(S,S)-[1-[5-(4-acetylamino-phenoxy)-1H-indol-3-ylmethyl]-2-(2-cyano-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

(S,S)-{2-(2-carbamoyl-pyrrolidin-1-yl)-1-[5-(4-nitro-phenoxy)-1H-indol-3-ylmethyl]-2-oxo-ethyl}-carbamic acid tert-butyl ester

(S,S)-4-{3-[2-tert-butoxycarbonylamino-3-(2-cyano-pyrrolidin-1-yl)-3-oxo-propyl]-1H-indol-5-yloxy}-benzoic acid

(S,S)-{2-(2-carbamoyl-pyrrolidin-1-yl)-1-{5-(4-formyl-phenoxy)-1H-indol-3-ylmethyl}-2-oxo-ethyl}-carbamic acid tert-butyl ester

Refernces

• 1、 -. "HIGHLY EFFICIENT MYELOPEROXIDASE ACTIVATABLE IMAGING AGENTS". Page/Page column 50; 51. . Retrieved 2021/06/26.
• 2、 Reinfelds, Matiss,Kalinins, Konstantins,Katkevica, Dace,Zemribo, Ronalds,Katkevics, Martins. "Synthesis of tryptophans by alkylation of chiral glycine enolate equivalents with quaternary gramines". supporting information. p. 5882 - 5885. Retrieved 2015/11/02.