(2S,3R,4S)-2,3-dimethoxy-4-((4-methoxybenzyl)oxy)-3,4-dihydrodibenzo[b,d]furan-1(2H)-one

Base Information

• Chemical Name: (2S,3R,4S)-2,3-dimethoxy-4-((4-methoxybenzyl)oxy)-3,4-dihydrodibenzo[b,d]furan-1(2H)-one
• CAS No.: 1514824-00-0
• Molecular Formula: C₂₂H₂₂O₆
• Molecular Weight: 382.413
• Mol file: 1514824-00-0.mol

Synonyms:(2S,3R,4S)-2,3-dimethoxy-4-((4-methoxybenzyl)oxy)-3,4-dihydrodibenzo[b,d]furan-1(2H)-one

Chemical Property of (2S,3R,4S)-2,3-dimethoxy-4-((4-methoxybenzyl)oxy)-3,4-dihydrodibenzo[b,d]furan-1(2H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S)-2,3-dimethoxy-4-((4-methoxybenzyl)oxy)-3,4-dihydrodibenzo[b,d]furan-1(2H)-one

There total 12 articles about (2S,3R,4S)-2,3-dimethoxy-4-((4-methoxybenzyl)oxy)-3,4-dihydrodibenzo[b,d]furan-1(2H)-one 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: 76.0%

(2S,3S,4S)-2-hydroxy-3-methoxy-4-((4-methoxybenzyl)oxy)-3,4-dihydrodibenzo[b,d]furan-1(2H)-one + methyl iodide (74-88-4) → (2S,3R,4S)-2,3-dimethoxy-4-((4-methoxybenzyl)oxy)-3,4-dihydrodibenzo[b,d]furan-1(2H)-one (1514824-00-0)

Guidance literature:

With silver(l) oxide; In tetrahydrofuran; for 24h; Inert atmosphere; Sealed tube; Heating;

DOI:10.1021/acs.joc.9b02171

Reference yield: 48.0%

C22H24O5 (1514823-98-3) → (2S,3R,4S)-2,3-dimethoxy-4-((4-methoxybenzyl)oxy)-3,4-dihydrodibenzo[b,d]furan-1(2H)-one (1514824-00-0)

Guidance literature:

C₂₂H₂₄O₅; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 18 ℃; for 14h;

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.33h;

DOI:10.1021/ol403220t

Reference yield:

C10H15BrO4 (1514823-88-1) → (2S,3R,4S)-2,3-dimethoxy-4-((4-methoxybenzyl)oxy)-3,4-dihydrodibenzo[b,d]furan-1(2H)-one (1514824-00-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

1.2: 4 h / 18 °C

2.1: acetic acid; water / 14 h / 70 °C

3.1: toluene-4-sulfonic acid / dichloromethane; water / 2 h / 0 °C

3.2: 6 h / -78 °C / Inert atmosphere

4.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; triethylamine / tetrahydrofuran; water / 2.5 h / 70 °C / Inert atmosphere

5.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 18 °C

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 14 h / 0 - 18 °C

6.2: 0.33 h / -78 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; water; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; mineral oil; 4.1: |Suzuki-Miyaura Coupling / 5.1: |Mitsunobu Displacement / 6.2: |Swern Oxidation;

DOI:10.1021/ol403220t

upstream raw materials:

C₁₀H₁₅BrO₄

(1R,2S,5S,6R)-3,6-dibromo-1,2-O-isopropylidenecyclohex-3-ene-1,2,5-triol

C₁₁H₁₇BrO₄

C₈H₁₃BrO₄