(4S,5S)-4-[3-(4-methoxybenzyloxy)propyl]-2-phenyl-1,3-dioxan-5-ol

Base Information

• Chemical Name: (4S,5S)-4-[3-(4-methoxybenzyloxy)propyl]-2-phenyl-1,3-dioxan-5-ol
• CAS No.: 831228-11-6
• Molecular Formula: C₂₁H₂₆O₅
• Molecular Weight: 358.434
• Mol file: 831228-11-6.mol

Synonyms:

Chemical Property of (4S,5S)-4-[3-(4-methoxybenzyloxy)propyl]-2-phenyl-1,3-dioxan-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-[3-(4-methoxybenzyloxy)propyl]-2-phenyl-1,3-dioxan-5-ol

There total 6 articles about (4S,5S)-4-[3-(4-methoxybenzyloxy)propyl]-2-phenyl-1,3-dioxan-5-ol 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:

p-Methoxybenzyl bromide (2746-25-0) → (4S,5S)-4-[3-(4-methoxybenzyloxy)propyl]-2-phenyl-1,3-dioxan-5-ol (831228-11-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / sodium hydride / tetrahydrofuran / 0 °C

2: 71 percent / pyridinium chlorochromate; sodium acetate; celite / CH₂Cl₂ / 6 h / 20 °C

3: 80 percent / benzene / 4 h / Heating

4: 80 percent / DIBAL-H / CH₂Cl₂ / 1 h / 20 °C

5: potassium ferricyanide; methanesulfonamide; K₂CO₃ / osmium tetraoxide; 1,4-bis(dihydroquinin-9-O-yl)phthalazine / 2-methyl-propan-2-ol; H₂O; toluene / 18 h / 0 °C

6: p-TsOH / CH₂Cl₂ / 20 °C

With methanesulfonamide; Celite; sodium acetate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; pyridinium chlorochromate; potassium hexacyanoferrate(III); (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol; benzene; 3: Wittig reaction / 5: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo0485381

Reference yield:

4-((4-methoxybenzyl)oxy)butanal (119649-27-3) → (4S,5S)-4-[3-(4-methoxybenzyloxy)propyl]-2-phenyl-1,3-dioxan-5-ol (831228-11-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / benzene / 4 h / Heating

2: 80 percent / DIBAL-H / CH₂Cl₂ / 1 h / 20 °C

3: potassium ferricyanide; methanesulfonamide; K₂CO₃ / osmium tetraoxide; 1,4-bis(dihydroquinin-9-O-yl)phthalazine / 2-methyl-propan-2-ol; H₂O; toluene / 18 h / 0 °C

4: p-TsOH / CH₂Cl₂ / 20 °C

With methanesulfonamide; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; potassium hexacyanoferrate(III); (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; osmium(VIII) oxide; In dichloromethane; water; toluene; tert-butyl alcohol; benzene; 1: Wittig reaction / 3: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo0485381

Reference yield:

4-(p-methoxybenzyloxy)butan-1-ol (119649-45-5) → (4S,5S)-4-[3-(4-methoxybenzyloxy)propyl]-2-phenyl-1,3-dioxan-5-ol (831228-11-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 71 percent / pyridinium chlorochromate; sodium acetate; celite / CH₂Cl₂ / 6 h / 20 °C

2: 80 percent / benzene / 4 h / Heating

3: 80 percent / DIBAL-H / CH₂Cl₂ / 1 h / 20 °C

4: potassium ferricyanide; methanesulfonamide; K₂CO₃ / osmium tetraoxide; 1,4-bis(dihydroquinin-9-O-yl)phthalazine / 2-methyl-propan-2-ol; H₂O; toluene / 18 h / 0 °C

5: p-TsOH / CH₂Cl₂ / 20 °C

With methanesulfonamide; Celite; sodium acetate; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; pyridinium chlorochromate; potassium hexacyanoferrate(III); (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; osmium(VIII) oxide; In dichloromethane; water; toluene; tert-butyl alcohol; benzene; 2: Wittig reaction / 4: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo0485381

upstream raw materials:

benzaldehyde dimethyl acetal

(2S,3S)-6-(4-methoxybenzyloxy)hexane-1,2,3-triol

p-Methoxybenzyl bromide

4-(p-methoxybenzyloxy)butan-1-ol

Downstream raw materials:

Methanesulfonic acid (4S,5S)-4-[3-(4-methoxy-benzyloxy)-propyl]-2-phenyl-[1,3]dioxan-5-yl ester

(4S,5R)-5-azido-4-[3-(4-methoxybenzyloxy)propyl]-2-phenyl-1,3-dioxane

Methanesulfonic acid 3-((4S,5R)-5-azido-2-phenyl-[1,3]dioxan-4-yl)-propyl ester

3-((4S,5R)-5-Azido-2-phenyl-[1,3]dioxan-4-yl)-propan-1-ol