52616-82-7

Usage

Uses

Used in Dietary Supplements:
L-Tyrosine, O-(1,1-dimethylethyl)-, methyl ester is used as a cognitive enhancer to improve mental performance, alertness, and reduce stress levels in individuals.
Used in Cosmetic and Skin Care Industry:
L-Tyrosine, O-(1,1-dimethylethyl)-, methyl ester is used as an antioxidant and anti-aging agent in cosmetic and skin care products to promote healthy and youthful skin.
Used in Pharmaceutical and Medicine Industry:
L-Tyrosine, O-(1,1-dimethylethyl)-, methyl ester has potential applications in the pharmaceutical and medicine fields due to its ability to support neurotransmitter production and regulation, which may contribute to the development of treatments for various conditions.

Upstream product

• 60-18-4 L-tyrosine 
• 13512-31-7 N-(benzyloxycarbonyl)-L-tyrosine methyl ester 
• 1080-06-4 L-Tyr-OMe 
• 5068-29-1 2-benzyloxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionic acid methyl ester 

Downstream Products

• 121772-99-4 (R)-N-Cbz-2-allylprolyl(O-tert-butyl)tyrosine methyl ester 
• 148080-99-3 (S)-2-{(S)-2-[(S)-2-(4-tert-Butoxy-phenyl)-1-methoxycarbonyl-ethylamino]-propionylamino}-3-phenyl-propionic acid benzyl ester 
• 1187890-76-1 C₂₇H₃₁F₃N₂O₅ 
• 958959-88-1 C₃₇H₅₇N₅O₉ 
• 958959-76-7 C₄₀H₆₄N₆O₉ 
• 958959-79-0 C₃₈H₅₉N₅O₉ 
• 958947-50-7 C₃₆H₅₇N₅O₈ 
• 1262482-89-2 C₃₄H₄₆N₄O₈ 
• 1262482-90-5 C₃₇H₅₃N₅O₈ 
• 1262482-91-6 C₃₅H₄₈N₄O₈ 

Relevant academic research and scientific papers

Flexible and convergent total synthesis of cyclotheonamide B

A convergent approach using two key intermediates, segment A [a L-proline-L-α-hydroxy-β-homoarginine-D-phenylalamine (Pro-hArg-D-Phe) tripeptide] and segment B [a vinylogous L-tyrosine-L-2,3-diaminopropanoic acid (vTyr-Dpr) dipeptide], was developed for the synthesis of cyclotheonamide B. The starting compound for the preparation of the hArg moiety 7, the predominant part of segment A, was N(α)-(benzyloxycarbonyl)-N(ω),N(ω)'-bis(tert-butyloxycarbonyl)-l-ar ginine methyl ester (15), which was converted into the aldehyde 16 and subsequently homologated using [tris(methylthio)methyl]lithium as a carboxylic acid anion equivalent. Coupling with properly protected Pro and D-Phe derivatives gave smoothly the desired Pro-hArg-D-Phe tripeptide derivative 24. The key feature of segment B, i.e., the L-tyrosine-derived α,β-unsaturated γ-amino acid 4, was prepared by a Wadsworth-Emmons olefination of the aldehyde 29 derived from N-(tert-butyloxycarbonyl), O-tert-butyl-L-tyrosine methyl ester (28). Selective N-(tert-butyloxycarbonyl) removal in the presence of the aryl tert-butyl ether present in the fully protected segment B, i.e., 32, was achieved by treatment with trimethylsilyl triflate/2,6-lutidine to give vTyr-Dpr dipeptide derivative 34 in quantitative yield. Coupling of the key intermediates 24 and 34 using 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) afforded the protected linear pentapeptide 35 in high yield. Treatment of 35 with Pd(PPh3)4/morpholine resulted in simultaneous removal of the C-terminal allyl group and the N-terminal allyloxycarbonyl group to yield 36. Ring closure was effected under dilution conditions by treatment with TBTU/1-hydroxybenzotriazole/4-(dimethylamino)pyridine and gave the protected cyclopentapeptide 37 in 61% yield. Oxidation of the hydroxyl group with Dess-Martin periodinane (24 h, 40°C) in the presence of tert-butyl alcohol gave 38, which was then subjected to O,N-deprotection with trifluoroacetic acid/thioanisole. Subsequent HPLC purification afforded cyclotheonamide B in an overall yield of 1.8% in 17 steps.

Total synthesis of cyclotheonamide B, a facile route towards analogues

A flexible, convergent synthesis of cyclotheonamide B (1b) was developed, starting from the constituent amino acids, using conventional benzyl-, t-butyl- and allyl-based protecting groups. By modification of the key intermediates, this approach allows the preparation of cyclotheonamide analogues.