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

Base Information

• Chemical Name: (4'S)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl azide
• CAS No.: 133008-62-5
• Molecular Formula: C₂₂H₂₂N₄O₂
• Molecular Weight: 375.434
• Mol file: 133008-62-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (4'S)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl azide 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: 90.0%

(4'R)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl chloride (133008-67-0) → (4'S)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl azide (133008-62-5)

Guidance literature:

With sodium azide; 15-crown-5; In tetrahydrofuran; at 70 ℃;

DOI:10.1021/jo00008a071

Reference yield:

5'-O-benzylpyridoxine (26864-21-1) → (4'S)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl azide (133008-62-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 83 percent / NaOMe / methanol / 0.33 h / Ambient temperature

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

3: 82 percent / 1 M aq. KMnO₄, 5percent aq. sodium phosphate / methanol / 1 h / Ambient temperature

4: 89 percent / diethyl ether; methanol / 0 °C

5: 93 percent / LiAlD₄ / tetrahydrofuran / 3 h / 0 °C

6: 93 percent / pyridinium chlorochromate, NaOAc, 3 Angstroem molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

7: 82 percent / R-Alpine-Borane / tetrahydrofuran / 0 °C

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

9: 90 percent / NaN₃, 15-crown-5 / tetrahydrofuran / 70 °C

With potassium permanganate; 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; triethylamine; sodium phosphate; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo00008a071

Reference yield:

3,5'-O-dibenzylpyridoxal (26866-40-0) → (4'S)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl azide (133008-62-5)

Guidance literature:

Multi-step reaction with 7 steps

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

2: 89 percent / diethyl ether; methanol / 0 °C

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

4: 93 percent / pyridinium chlorochromate, NaOAc, 3 Angstroem molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

5: 82 percent / R-Alpine-Borane / tetrahydrofuran / 0 °C

6: 75 percent / SOCl₂, triethylamine / CH₂Cl₂ / 8 h / Ambient temperature

7: 90 percent / NaN₃, 15-crown-5 / tetrahydrofuran / 70 °C

With potassium permanganate; thionyl chloride; sodium azide; lithium aluminium deuteride; B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; 15-crown-5; 3 A molecular sieve; sodium acetate; triethylamine; sodium phosphate; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo00008a071

upstream raw materials:

(4'S)-<4'-2H1>-3,5'-O-dibenzylpyridoxine

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

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

5'-O-benzylpyridoxine

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

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

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

Refernces