(5S,6R)-5-(benzyloxy)-4-methoxy-6-phenethyl-5,6-dihydro-2H-2-pyranone

Base Information

• Chemical Name: (5S,6R)-5-(benzyloxy)-4-methoxy-6-phenethyl-5,6-dihydro-2H-2-pyranone
• CAS No.: 955361-49-6
• Molecular Formula: C₂₁H₂₂O₄
• Molecular Weight: 338.403
• Mol file: 955361-49-6.mol

Synonyms:(5S,6R)-5-(benzyloxy)-4-methoxy-6-phenethyl-5,6-dihydro-2H-2-pyranone

Chemical Property of (5S,6R)-5-(benzyloxy)-4-methoxy-6-phenethyl-5,6-dihydro-2H-2-pyranone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6R)-5-(benzyloxy)-4-methoxy-6-phenethyl-5,6-dihydro-2H-2-pyranone

There total 7 articles about (5S,6R)-5-(benzyloxy)-4-methoxy-6-phenethyl-5,6-dihydro-2H-2-pyranone 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: 75.0%

(4S,5R)-4-benzyloxy-5-hydroxy-3-oxo-7-phenylheptanoic acid ethyl ester (955361-48-5) + dimethyl sulfate (77-78-1) → (5S,6R)-5-(benzyloxy)-4-methoxy-6-phenethyl-5,6-dihydro-2H-2-pyranone (955361-49-6)

Guidance literature:

(4S,5R)-4-benzyloxy-5-hydroxy-3-oxo-7-phenylheptanoic acid ethyl ester; With potassium carbonate; In methanol; for 2h;

dimethyl sulfate; In acetone; for 10h; Further stages.;

DOI:10.1016/j.tetasy.2007.07.032

Reference yield:

C20H20O4 + dimethyl sulfate (77-78-1) → (5S,6R)-5-(benzyloxy)-4-methoxy-6-phenethyl-5,6-dihydro-2H-2-pyranone (955361-49-6)

Guidance literature:

With potassium carbonate; In acetone; at 0 ℃; for 10h;

DOI:10.1016/j.tetasy.2009.08.006

Reference yield:

(2R,3R)-2-benzyloxy-3-(4-methoxybenzyloxy)-5-phenylpentan-1-ol (955361-45-2) → (5S,6R)-5-(benzyloxy)-4-methoxy-6-phenethyl-5,6-dihydro-2H-2-pyranone (955361-49-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Dess-Martin periodinate / CH₂Cl₂ / 1 h / 0 °C

2.1: 80 percent / SnCl₂ / CH₂Cl₂ / 1 h / 0 °C

3.1: 85 percent / ZrCl₄ / acetonitrile / 2 h / 20 °C

4.1: K₂CO₃ / methanol / 2 h

4.2: 75 percent / acetone / 10 h

With zirconium(IV) chloride; potassium carbonate; Dess-Martin periodane; tin(ll) chloride; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/j.tetasy.2007.07.032

upstream raw materials:

(4S,5R)-4-benzyloxy-5-hydroxy-3-oxo-7-phenylheptanoic acid ethyl ester

dimethyl sulfate

(5R,6R)-5-benzyloxy-2-(4-methoxyphenyl)-6-phenethyl-[1,3]dioxan

(2R,3R)-2-benzyloxy-3-(4-methoxybenzyloxy)-5-phenylpentan-1-ol

Downstream raw materials:

(5R,6S)-5-hydroxy-4-methoxy-6-phenethyl-5,6-dihydro-2H-pyran-2-one