Tyrosine, b-hydroxy-O-(methoxymethyl)-

Base Information

• Chemical Name: Tyrosine, b-hydroxy-O-(methoxymethyl)-
• CAS No.: 125774-95-0
• Molecular Formula: C11H15NO5
• Molecular Weight: 241.244
• Mol file: 125774-95-0.mol

Synonyms:

Chemical Property of Tyrosine, b-hydroxy-O-(methoxymethyl)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Tyrosine, b-hydroxy-O-(methoxymethyl)-

There total 1 articles about Tyrosine, b-hydroxy-O-(methoxymethyl)- 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:

4-methoxymethoxy-benzaldehyde (6515-21-5) + glycine (56-40-6,18875-39-3,25718-94-9) → O-methoxymethyl-β-hydroxytyrosine (125774-95-0)

Guidance literature:

With potassium hydroxide; In ethanol; for 19h; Yield given; Ambient temperature;

DOI:10.1248/cpb.45.236

Reference yield:

O-methoxymethyl-β-hydroxytyrosine (125774-95-0) → O-methoxymethyl-N-methyl-β-hydroxytyrosine (125774-96-1)

Guidance literature:

In 1N-sodium hydroxide;

Reference yield:

O-methoxymethyl-β-hydroxytyrosine (125774-95-0) → WS9326A (125774-71-2)

Guidance literature:

Multi-step reaction with 23 steps

1: 1 N aq. NaOH / 0.33 h / 90 °C

2: 85 percent / BSA / CH₂Cl₂ / 5 h / 0 - 20 °C

3: 32.1 percent / diethyl ether; ethyl acetate / 0.17 h

4: 93.6 percent / Et₃N, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

5: 72.1 percent / thiophenol, TFA / CH₂Cl₂ / 0.5 h / 0 °C

6: 49.1 percent / 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline / CH₂Cl₂ / 14 h / Ambient temperature

7: DBU / toluene / 2.5 h / Ambient temperature

8: 98 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

9: 87.3 percent / NaOH / methanol / 48 h / 30 °C

10: 32.6 percent / Et₃N, EEDQ / CH₂Cl₂ / 33 h / Ambient temperature

11: 21.2 percent / acetone; toluene / 1.5 h / 0 °C / Irradiation

12: 99.9 percent / 67percent AcOH / 28 h / 25 °C

13: 86.5 percent / EDC*HCl, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

14: 4 N HCl, anisole / dioxane / 0.5 h / Ambient temperature

15: Et₃N, HOBT, EDC*HCl / CH₂Cl₂ / 1 h / Ambient temperature

16: 4 N HCl, anisole / dioxane / 0.5 h / Ambient temperature

17: Et₃N, HOBT, EDC*HCl / CH₂Cl₂ / 8 h / Ambient temperature

18: 82.6 percent / Zn, 90percent AcOH / Ambient temperature

19: EDC*HCl / CH₂Cl₂; dimethylformamide / Ambient temperature

20: TFA, anisole / 0.5 h / Ambient temperature

21: pyridine / dimethylformamide / 16 h / Ambient temperature

22: 74.9 percent / HF, pyridine, anisole / 1 h / Ambient temperature

23: 2.7 percent / BSA, DMAP / CH₂Cl₂; dimethylformamide / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; benzenesulfonamide; dmap; sodium hydroxide; hydrogen fluoride; benzotriazol-1-ol; acetic acid; thiophenol; methoxybenzene; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; zinc; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1248/cpb.45.236

upstream raw materials:

4-methoxymethoxy-benzaldehyde

glycine

Downstream raw materials:

WS₉₃₂₆A

C₅₉H₇₁N₉O₁₇

Cbz-Thr[Boc-allo-Thr-Asn-Ser(Bzl)]-(E)ΔMeTyr-Leu-D-Phe-OTce

C₆₄H₇₉N₉O₁₉

Refernces

• 1、 -. "Cyclic peptide antagonists of Substance P and Substance K". . . Retrieved 2008/06/13.