(4'R)-<4'-2H1>-3,5'-O-dibenzylpyridoxamine

Base Information

• Chemical Name: (4'R)-<4'-2H1>-3,5'-O-dibenzylpyridoxamine
• CAS No.: 133008-69-2
• Molecular Formula: C₂₂H₂₄N₂O₂
• Molecular Weight: 349.437
• Mol file: 133008-69-2.mol

Synonyms:

Chemical Property of (4'R)-<4'-2H1>-3,5'-O-dibenzylpyridoxamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4'R)-<4'-2H1>-3,5'-O-dibenzylpyridoxamine

There total 17 articles about (4'R)-<4'-2H1>-3,5'-O-dibenzylpyridoxamine 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'S)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl azide (133008-62-5) → (4'S)-<4'-2H1>-3,5'-O-dibenzylpyridoxamine (133008-68-1) + (4'R)-<4'-2H1>-3,5'-O-dibenzylpyridoxamine (133008-69-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; Title compound not separated from byproducts;

DOI:10.1021/jo00008a071

Reference yield:

(4'R)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl azide (133008-63-6) → (4'S)-<4'-2H1>-3,5'-O-dibenzylpyridoxamine (133008-68-1) + (4'R)-<4'-2H1>-3,5'-O-dibenzylpyridoxamine (133008-69-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; Title compound not separated from byproducts;

DOI:10.1021/jo00008a071

Reference yield:

5-hydroxy-6-methyl-3,4-pyridinedimethanol (65-23-6) → (4'R)-<4'-2H1>-3,5'-O-dibenzylpyridoxamine (133008-69-2)

Guidance literature:

Multi-step reaction with 13 steps

1: 83 percent / p-TsOH / acetone / 16 h

2: 1) NaH / 1) THF, 30 min, reflux, 2) 4 h, reflux

3: 94 percent / 98percent formic acid / H₂O / 24 h / 50 °C

4: 83 percent / NaOMe / methanol / 0.33 h / Ambient temperature

5: 94 percent / pyridinium chlorochromate, NaOAc, 3 Angstroem molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

6: 82 percent / 1 M aq. KMnO₄, 5percent aq. sodium phosphate / methanol / 1 h / Ambient temperature

7: 89 percent / diethyl ether; methanol / 0 °C

8: 93 percent / LiAlD₄ / tetrahydrofuran / 3 h / 0 °C

9: 93 percent / pyridinium chlorochromate, NaOAc, 3 Angstroem molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

10: 82 percent / R-Alpine-Borane / tetrahydrofuran / 0 °C

11: 75 percent / SOCl₂, triethylamine / CH₂Cl₂ / 8 h / Ambient temperature

12: 90 percent / NaN₃, 15-crown-5 / tetrahydrofuran / 70 °C

13: LiAlH₄ / tetrahydrofuran / 0 °C

With potassium permanganate; lithium aluminium tetrahydride; formic acid; thionyl chloride; sodium azide; lithium aluminium deuteride; B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; 15-crown-5; 3 A molecular sieve; sodium methylate; sodium acetate; sodium hydride; toluene-4-sulfonic acid; triethylamine; sodium phosphate; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone;

DOI:10.1021/jo00008a071

upstream raw materials:

(4'S)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl azide

(4'R)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl azide

(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol

5-hydroxy-6-methyl-3,4-pyridinedimethanol

Downstream raw materials:

4'-N-camphanyl-(4'R)-<4-2H1>-3,5'-O-dibenzylpyridoxamine

4'-N-camphanyl-(4'S)-<4-2H1>-3,5'-O-dibenzylpyridoxamine

Refernces