(1R,2R)-1-(4-benzyloxy-3-methoxyphenyl)-2,3-dihydroxypropanol

Base Information

• Chemical Name: (1R,2R)-1-(4-benzyloxy-3-methoxyphenyl)-2,3-dihydroxypropanol
• CAS No.: 300678-35-7
• Molecular Formula: C₁₇H₂₀O₅
• Molecular Weight: 304.343
• Mol file: 300678-35-7.mol

Synonyms:(1R,2R)-1-(4-benzyloxy-3-methoxyphenyl)-2,3-dihydroxypropanol

Chemical Property of (1R,2R)-1-(4-benzyloxy-3-methoxyphenyl)-2,3-dihydroxypropanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-1-(4-benzyloxy-3-methoxyphenyl)-2,3-dihydroxypropanol

There total 8 articles about (1R,2R)-1-(4-benzyloxy-3-methoxyphenyl)-2,3-dihydroxypropanol 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: 94.0%

(2E)-3-(4-O-benzyloxy-3-methoxyphenyl)prop-2-en-1-ol (38153-27-4) → (1R,2R)-1-(4-benzyloxy-3-methoxyphenyl)-2,3-dihydroxypropanol (300678-35-7)

Guidance literature:

With methanesulfonamide; AD-mix-β; water; In tert-butyl alcohol; at 0 ℃; optical yield given as %ee;

DOI:10.1007/s00706-010-0420-3

Reference yield:

(2E)-3-(4-O-benzyloxy-3-methoxyphenyl)prop-2-en-1-ol (38153-27-4) → (1S,2S)-1-(4-benzyloxy-3-methoxyphenyl)-2,3-dihydroxypropanol (213595-71-2) + (1R,2R)-1-(4-benzyloxy-3-methoxyphenyl)-2,3-dihydroxypropanol (300678-35-7)

Guidance literature:

With AD-mix-α; water; In tert-butyl alcohol; at 0 ℃; for 20h; Title compound not separated from byproducts;

DOI:10.1016/S0040-4039(00)00820-0

Reference yield:

Methyl ferulate (2309-07-1) → (1R,2R)-1-(4-benzyloxy-3-methoxyphenyl)-2,3-dihydroxypropanol (300678-35-7)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / dimethylformamide / 3 h / 160 °C

2: 88 percent / LiAlH₄ / tetrahydrofuran / 1 h / -10 °C

3: AD-mix-β; MeSO2NH2; H2O / 2-methyl-propan-2-ol / 20 h / 0 °C

With lithium aluminium tetrahydride; methanesulfonamide; AD-mix-β; water; potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Alkylation / 2: Reduction / 3: dihydroxylation;

DOI:10.1016/S0957-4166(00)00234-2

upstream raw materials:

(2E)-3-(4-O-benzyloxy-3-methoxyphenyl)prop-2-en-1-ol

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Methyl ferulate

methyl (E)-3-[4-(benzyloxy)-3-methoxyphenyl]acrylate

Downstream raw materials:

threo-(1R,2R)-1-(4-benzyloxy-3-methoxyphenyl)-2,3-epoxy-1-propanol

threo-(1R,2R)-1-(4-benzyloxy-3-methoxyphenyl)-3-O-tosyl-1,2,3-propanetriol

threo-(1R,2R)-1-[3-methoxy-4-(methoxymethoxy)phenyl]-1-(2,3,4,5-tetrahydropyran-2-yloxy)-2-propanol

(-)?erythro?(7S,8R)?Δ^8′?4,7?dihydroxy?3,3',5'-tetramethoxy?8?O?4′?neolignan