(2R,3R)-4-benzyloxy-3-hydroxy-2-(4-methoxyphenyl)butanoic acid

Base Information

• Chemical Name: (2R,3R)-4-benzyloxy-3-hydroxy-2-(4-methoxyphenyl)butanoic acid
• CAS No.: 461644-54-2
• Molecular Formula: C₁₈H₂₀O₅
• Molecular Weight: 316.354
• Mol file: 461644-54-2.mol

Synonyms:(2R,3R)-4-benzyloxy-3-hydroxy-2-(4-methoxyphenyl)butanoic acid

Chemical Property of (2R,3R)-4-benzyloxy-3-hydroxy-2-(4-methoxyphenyl)butanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-4-benzyloxy-3-hydroxy-2-(4-methoxyphenyl)butanoic acid

There total 6 articles about (2R,3R)-4-benzyloxy-3-hydroxy-2-(4-methoxyphenyl)butanoic 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: 99.0%

(R)-4-Benzyl-3-[(2R,3R)-4-benzyloxy-3-hydroxy-2-(4-methoxy-phenyl)-butyryl]-oxazolidin-2-one (570375-92-7) → (2R,3R)-4-benzyloxy-3-hydroxy-2-(4-methoxyphenyl)butanoic acid (461644-54-2)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 1h;

DOI:10.1016/S0960-894X(03)00131-8

Reference yield: 82.0%

(2S,4R,5R)-1,2-O-cyclohexylidene-6-O-benzyl-1,2,5,6-tetrahydroxy-4-(4-methoxyphenyl)hexan-3-one (461644-53-1) → (2R,3R)-4-benzyloxy-3-hydroxy-2-(4-methoxyphenyl)butanoic acid (461644-54-2)

Guidance literature:

(2S,4R,5R)-1,2-O-cyclohexylidene-6-O-benzyl-1,2,5,6-tetrahydroxy-4-(4-methoxyphenyl)hexan-3-one; With periodic acid; In diethyl ether; ethyl acetate; at 20 ℃;

With potassium hydrogencarbonate; In methanol; at 20 ℃; for 2h;

DOI:10.1016/S0957-4166(02)00227-6

Reference yield:

benzyloxyacetoaldehyde (60656-87-3) → (2R,3R)-4-benzyloxy-3-hydroxy-2-(4-methoxyphenyl)butanoic acid (461644-54-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂BOTf; i-Pr₂EtN / 0.5 h / 0 °C

1.2: SnCl₄ / 3 h / -78 °C

2.1: 99 percent / H₂O₂; LiOH / tetrahydrofuran; H₂O / 1 h / 0 °C

With lithium hydroxide; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water;

DOI:10.1016/S0960-894X(03)00131-8

upstream raw materials:

(2S,4R,5R)-1,2-O-cyclohexylidene-6-O-benzyl-1,2,5,6-tetrahydroxy-4-(4-methoxyphenyl)hexan-3-one

(R)-4-Benzyl-3-[(2R,3R)-4-benzyloxy-3-hydroxy-2-(4-methoxy-phenyl)-butyryl]-oxazolidin-2-one

benzyloxyacetoaldehyde

(R)-4-benzyl-3-(2-(4-methoxyphenyl)acetyl)oxazolidin-2-one

Downstream raw materials:

(4R,5R)-5-benzyloxymethyl-4-(4-methoxyphenyl)oxazolidin-2-one