(3R,4S)-3,4-dihydroxy-3-(3,4-dimethoxybenzyl)-7-methoxychroman

Base Information

• Chemical Name: (3R,4S)-3,4-dihydroxy-3-(3,4-dimethoxybenzyl)-7-methoxychroman
• CAS No.: 111254-23-0
• Molecular Formula: C₁₉H₂₂O₆
• Molecular Weight: 346.38
• Mol file: 111254-23-0.mol

Synonyms:(3R,4S)-3,4-dihydroxy-3-(3,4-dimethoxybenzyl)-7-methoxychroman

Chemical Property of (3R,4S)-3,4-dihydroxy-3-(3,4-dimethoxybenzyl)-7-methoxychroman

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-3,4-dihydroxy-3-(3,4-dimethoxybenzyl)-7-methoxychroman

There total 38 articles about (3R,4S)-3,4-dihydroxy-3-(3,4-dimethoxybenzyl)-7-methoxychroman 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: 100.0%

3-(3,4-dimethoxybenzyl)-7-methoxy-2H-chromene → (3RS,4SR)-3,4-dihydroxy-3-(3,4-dimethoxybenzyl)-7-methoxychroman (94385-81-6,111254-23-0,111254-24-1,111321-33-6,111321-34-7)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 0 ℃; for 3h;

DOI:10.1039/c5ob00216h

Reference yield: 91.0%

(R)-(-)-O-trimethylsappanone B (113122-58-0) → (3R,4S)-3,4-dihydroxy-3-(3,4-dimethoxybenzyl)-7-methoxychroman (111254-23-0)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 2h; Ambient temperature;

DOI:10.1021/jo00059a026

Reference yield:

3-(3,4-dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)-1-propanone (76672-90-7) → (3R,4S)-3,4-dihydroxy-3-(3,4-dimethoxybenzyl)-7-methoxychroman (111254-23-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / sodium sand / Ambient temperature

2: 98 percent / H₂ / 10 percent Pd/C / ethyl acetate / 4 h / 1292.9 Torr

3: 1) NaHMDS, 2) (+)-8,8-dichlorocamphorylsuflonyl oxaziridine 7b / 1) THF, -78 deg C, 30 min, 2) 30 min

4: 91 percent / NaBH₄ / ethanol / 2 h / Ambient temperature

With sodium tetrahydroborate; sodium sand; hydrogen; sodium hexamethyldisilazane; (+)-[(8,8-dichlorocamphoryl)sulfonyl]oxaziridine; palladium on activated charcoal; In ethanol; ethyl acetate;

DOI:10.1021/jo00059a026

upstream raw materials:

(3RS,4RS)-3-(4-hydroxy-3-methoxybenzyl)-3,4,7-trihydroxychroman <(+/-)-3'-O-methylepisappanol>

dimethyl sulfate

7-hydroxy-2,3-dihydro-4H-chromen-4-one

(E)-3-(4-hydroxy-3-methoxybenzylidene)-7-hydroxychroman-4-one

Downstream raw materials:

(3aR,9bS)-3a-(3,4-Dimethoxy-benzyl)-7-methoxy-2,2-dimethyl-3a,9b-dihydro-4H-[1,3]dioxolo[4,5-c]chromene

(R)-3-(3,4-Dimethoxy-benzyl)-7-methoxy-chroman-4-ol

Methanesulfonic acid (R)-3-(3,4-dimethoxy-benzyl)-7-methoxy-4-oxo-chroman-3-yl ester

(R)-3-(3,4-Dimethoxy-benzyl)-7-methoxy-chroman-4-one