(2S,3S)-2--N-methylamino>-3-hydroxy-3-(4-iodophenyl)propionic acid

Base Information

• Chemical Name: (2S,3S)-2--N-methylamino>-3-hydroxy-3-(4-iodophenyl)propionic acid
• CAS No.: 161634-78-2
• Molecular Formula: C₁₅H₂₀INO₅
• Molecular Weight: 421.232
• Mol file: 161634-78-2.mol

Synonyms:(2S,3S)-2--N-methylamino>-3-hydroxy-3-(4-iodophenyl)propionic acid

Chemical Property of (2S,3S)-2--N-methylamino>-3-hydroxy-3-(4-iodophenyl)propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2--N-methylamino>-3-hydroxy-3-(4-iodophenyl)propionic acid

There total 6 articles about (2S,3S)-2--N-methylamino>-3-hydroxy-3-(4-iodophenyl)propionic acid 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: 98.0%

di-tert-butyl dicarbonate (24424-99-5) + (2S,3S)-3-hydroxy-3-(4-iodophenyl)-2-(methylamino)propionic acid (161634-77-1) → (2S,3S)-2--N-methylamino>-3-hydroxy-3-(4-iodophenyl)propionic acid (161634-78-2)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; water; at 25 ℃; for 4h;

DOI:10.1021/ja00098a015

Reference yield:

(1S,2R)-1-(4-Iodo-phenyl)-2-methylamino-propane-1,3-diol (161634-84-0) → (2S,3S)-2--N-methylamino>-3-hydroxy-3-(4-iodophenyl)propionic acid (161634-78-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 46 percent / O₂ / Pt / acetone; H₂O / 12 h

2: 98 percent / K₂CO₃ / tetrahydrofuran; H₂O / 4 h / 25 °C

With oxygen; potassium carbonate; platinum; In tetrahydrofuran; water; acetone;

DOI:10.1021/ja00098a015

Reference yield:

trans-3-(4-iodophenyl)-2-propenoic acid ethyl ester (161634-73-7) → (2S,3S)-2--N-methylamino>-3-hydroxy-3-(4-iodophenyl)propionic acid (161634-78-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / DIBAL-H / CH₂Cl₂; hexane / 0.33 h / -78 °C

2: 1.) (+)-diisopropyl L-tartrate, Ti(O-i-Pr)4, 2.) t-BuOOH / 1.) CH₂Cl₂, -20 deg C, 30 min, 2.) CH₂Cl₂, -20 deg C, 4 h

3: 81 percent / PDC / dimethylformamide / 10 h / 25 °C

4: 2.) 3 N aq. HCl / 1.) H₂O, reflux, 4 h, 2.) 25 deg C, 30 min

5: 98 percent / K₂CO₃ / tetrahydrofuran; H₂O / 4 h / 25 °C

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dipyridinium dichromate; L-(+)-diisopropyl tartrate; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja00098a015

upstream raw materials:

di-tert-butyl dicarbonate

(2S,3S)-3-hydroxy-3-(4-iodophenyl)-2-(methylamino)propionic acid

trans-3-(4-iodophenyl)-2-propenoic acid ethyl ester

(2E)-3-(4-iodophenyl)-prop-2-en-1-ol

Downstream raw materials:

C₂₇H₄₈INO₅Si₂

(2S,3S)-3-<(tert-butyldimethylsilyl)oxy>-2--N-methylamino>-3-(4-iodophenyl)propionic acid

pentafluorophenyl (2S,3S)-3-<(tert-butyldimethylsilyl)oxy>-2--N-methylamino>-3-(4-iodophenyl)propionate

3-hydroxy-N,O⁴-dimethyl-N-<3(S)-<(tert-butyldimethylsilyl)oxy>-N-<(tert-butyloxy)carbonyl>-N-methyl-4'-iodo-L-phenylalanyl>-L-tyrosine methyl ester