(1S,2S)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol

Base Information

• Chemical Name: (1S,2S)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol
• CAS No.: 853786-31-9
• Molecular Formula: C₁₃H₂₀O₇
• Molecular Weight: 288.298
• Mol file: 853786-31-9.mol

Synonyms:(1S,2S)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol

Chemical Property of (1S,2S)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol

There total 4 articles about (1S,2S)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-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: 78.0%

(E)-3-(3,5-dimethoxy-4-(methoxymethoxy)phenyl)prop-2-en-1-ol (179122-39-5) → (1S,2S)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol (853786-31-9)

Guidance literature:

With AD-mix-α; methanesulfonamide; In water; tert-butyl alcohol; at 0 ℃; for 48h;

DOI:10.1016/j.tetasy.2005.02.035

Reference yield:

ethyl (E)-3,5-dimethoxy-4-(methoxymethoxy)-cinnamate (853786-20-6) → (1S,2S)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol (853786-31-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / DIBAL-H / toluene; hexane / -10 °C

2: 78 percent / AD mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 48 h / 0 °C

With AD-mix-α; methanesulfonamide; diisobutylaluminium hydride; In hexane; water; toluene; tert-butyl alcohol; 2: Sharpless asymmetric dihydroxylation;

DOI:10.1016/j.tetasy.2005.02.035

Reference yield:

3,5-dimethoxy-4-(methoxymethoxy)benzaldehyde (55211-66-0) → (1S,2S)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol (853786-31-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 0 - 18 °C

1.2: 83 percent / tetrahydrofuran / 4 h / 18 °C

2.1: 81 percent / DIBAL-H / toluene; hexane / -10 °C

3.1: 78 percent / AD mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 48 h / 0 °C

With AD-mix-α; methanesulfonamide; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; water; toluene; tert-butyl alcohol; 1.2: Horner-Wadsworth-Emmons / 3.1: Sharpless asymmetric dihydroxylation;

DOI:10.1016/j.tetasy.2005.02.035

upstream raw materials:

(E)-3-(3,5-dimethoxy-4-(methoxymethoxy)phenyl)prop-2-en-1-ol

ethyl (E)-3,5-dimethoxy-4-(methoxymethoxy)-cinnamate

3,5-dimethoxy-4-(methoxymethoxy)benzaldehyde

syringic aldehyde

Downstream raw materials:

(2S,3S)-6-[(E)-2-(3,5-Bis-methoxymethoxy-phenyl)-vinyl]-3-(3,5-dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine

(1'R,2'S)-4-benzyloxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde

(2S,3S)-3-(3,5-Dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde

(2R,3R)-3-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2-hydroxymethyl-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde

Refernces