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

Base Information

• Chemical Name: (4'R)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl (S)-(+)-O-acetylmandelate
• CAS No.: 133008-59-0
• Molecular Formula: C₃₂H₃₁NO₆
• Molecular Weight: 526.593
• Mol file: 133008-59-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about (4'R)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl (S)-(+)-O-acetylmandelate 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: 83.0%

(S)-acetylmandelic acid (7322-88-5) + (4'S)-<4'-2H1>-3,5'-O-dibenzylpyridoxine (133008-58-9) → (4'S)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl (S)-(+)-O-acetylmandelate (133008-60-3) + (4'R)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl (S)-(+)-O-acetylmandelate (133008-59-0)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; for 2h; Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/jo00008a071

Reference yield: 81.0%

(S)-acetylmandelic acid (7322-88-5) + (4'R)-<4'-2H1>-3,5'-O-dibenzylpyridoxine (133008-57-8) → (4'S)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl (S)-(+)-O-acetylmandelate (133008-60-3) + (4'R)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl (S)-(+)-O-acetylmandelate (133008-59-0)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; for 2h; Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/jo00008a071

Reference yield:

5'-O-benzylpyridoxine (26864-21-1) → (4'R)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl (S)-(+)-O-acetylmandelate (133008-59-0)

Guidance literature:

Multi-step reaction with 8 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: 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 2 h / Ambient temperature

With potassium permanganate; lithium aluminium deuteride; B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; 3 A molecular sieve; sodium methylate; sodium acetate; dicyclohexyl-carbodiimide; sodium phosphate; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo00008a071

upstream raw materials:

(S)-acetylmandelic acid

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

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

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