methyl (2S,3R)-2,3-dihydroxy-3-[3',4'-bis(methoxymethoxy)phenyl]propionate

Base Information

• Chemical Name: methyl (2S,3R)-2,3-dihydroxy-3-[3',4'-bis(methoxymethoxy)phenyl]propionate
• CAS No.: 455952-08-6
• Molecular Formula: C₁₄H₂₀O₈
• Molecular Weight: 316.308
• Mol file: 455952-08-6.mol

Synonyms:methyl (2S,3R)-2,3-dihydroxy-3-[3',4'-bis(methoxymethoxy)phenyl]propionate

Chemical Property of methyl (2S,3R)-2,3-dihydroxy-3-[3',4'-bis(methoxymethoxy)phenyl]propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,3R)-2,3-dihydroxy-3-[3',4'-bis(methoxymethoxy)phenyl]propionate

There total 2 articles about methyl (2S,3R)-2,3-dihydroxy-3-[3',4'-bis(methoxymethoxy)phenyl]propionate 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: 98.0%

(E)-methyl 3-(3,4-bis(methoxymethoxy)phenyl)acrylate (114590-76-0) → methyl (2S,3R)-2,3-dihydroxy-3-[3',4'-bis(methoxymethoxy)phenyl]propionate (455952-08-6)

Guidance literature:

With methanesulfonamide; AD-mix-β; In water; tert-butyl alcohol; at 20 ℃; for 5h;

DOI:10.1016/S0957-4166(02)00182-9

Reference yield:

Methyl caffeate (3843-74-1,67667-67-8) → methyl (2S,3R)-2,3-dihydroxy-3-[3',4'-bis(methoxymethoxy)phenyl]propionate (455952-08-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / NaH / dimethylformamide / 1 h / 20 °C

2: 98 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 5 h / 20 °C

With methanesulfonamide; AD-mix-β; sodium hydride; In water; N,N-dimethyl-formamide; tert-butyl alcohol; 2: Sharpless asymmetric dihydroxylation;

DOI:10.1016/S0957-4166(02)00182-9

Reference yield: 98.0%

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride (39637-99-5,20445-33-4) + methyl (2S,3R)-2,3-dihydroxy-3-[3',4'-bis(methoxymethoxy)phenyl]propionate (455952-08-6) → methyl (2S,3R)-2,3-bis[(S)-α-methoxy-α-(trifluoromethyl)phenylacetoxy]-3-[3',4'-bis(methoxymethoxy)phenyl]propionate

Guidance literature:

With dmap; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/S0957-4166(02)00182-9

upstream raw materials:

(E)-methyl 3-(3,4-bis(methoxymethoxy)phenyl)acrylate

Methyl caffeate