(4R,6R)-4-Allyl-6-((R)-2-benzyloxy-1-methyl-ethyl)-tetrahydro-pyran-2-one

Base Information

• Chemical Name: (4R,6R)-4-Allyl-6-((R)-2-benzyloxy-1-methyl-ethyl)-tetrahydro-pyran-2-one
• CAS No.: 909257-58-5
• Molecular Formula: C₁₈H₂₄O₃
• Molecular Weight: 288.387
• Mol file: 909257-58-5.mol

Synonyms:(4R,6R)-4-Allyl-6-((R)-2-benzyloxy-1-methyl-ethyl)-tetrahydro-pyran-2-one

Chemical Property of (4R,6R)-4-Allyl-6-((R)-2-benzyloxy-1-methyl-ethyl)-tetrahydro-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,6R)-4-Allyl-6-((R)-2-benzyloxy-1-methyl-ethyl)-tetrahydro-pyran-2-one

There total 7 articles about (4R,6R)-4-Allyl-6-((R)-2-benzyloxy-1-methyl-ethyl)-tetrahydro-pyran-2-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: 65.0%

(3R,5S,6R)-3-Allyl-7-benzyloxy-5-hydroxy-6-methyl-heptanoic acid methyl ester (909257-56-3) → (4R,6R)-4-Allyl-6-((R)-2-benzyloxy-1-methyl-ethyl)-tetrahydro-pyran-2-one (909257-58-5)

Guidance literature:

With potassium carbonate; diethylazodicarboxylate; 4-nitro-benzoic acid; In tetrahydrofuran; methanol;

DOI:10.1016/j.tetlet.2006.06.046

Reference yield:

Acrylic acid (S)-1-((R)-2-benzyloxy-1-methyl-ethyl)-but-3-enyl ester (909257-66-5) → (4R,6R)-4-Allyl-6-((R)-2-benzyloxy-1-methyl-ethyl)-tetrahydro-pyran-2-one (909257-58-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / Grubbs' catalyst

2: 85 percent / tetrahydrofuran / -78 - -40 °C

3: 100 percent / LiOH / methanol

4: 90 percent / CH₂Cl₂

5: 65 percent / 4-nitrobenzoic acid; DEAD; K₂CO₃ / tetrahydrofuran; methanol

With lithium hydroxide; potassium carbonate; diethylazodicarboxylate; 4-nitro-benzoic acid; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; 2: Michael reaction;

DOI:10.1016/j.tetlet.2006.06.046

Reference yield:

(R)-3-benzyloxy-2-methylpropanal (79026-61-2) → (4R,6R)-4-Allyl-6-((R)-2-benzyloxy-1-methyl-ethyl)-tetrahydro-pyran-2-one (909257-58-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / SnCl₄ / CH₂Cl₂ / -90 °C

2: 80 percent / Et₃N / CH₂Cl₂

3: 80 percent / Grubbs' catalyst

4: 85 percent / tetrahydrofuran / -78 - -40 °C

5: 100 percent / LiOH / methanol

6: 90 percent / CH₂Cl₂

7: 65 percent / 4-nitrobenzoic acid; DEAD; K₂CO₃ / tetrahydrofuran; methanol

With lithium hydroxide; tin(IV) chloride; potassium carbonate; triethylamine; diethylazodicarboxylate; 4-nitro-benzoic acid; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; 1: Mitsunobu reaction / 4: Michael reaction;

DOI:10.1016/j.tetlet.2006.06.046

upstream raw materials:

(3R,5S,6R)-3-Allyl-7-benzyloxy-5-hydroxy-6-methyl-heptanoic acid methyl ester

(S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-5,6-dihydro-pyran-2-one

Acrylic acid (S)-1-((R)-2-benzyloxy-1-methyl-ethyl)-but-3-enyl ester

(4R,6S)-4-Allyl-6-((R)-2-benzyloxy-1-methyl-ethyl)-tetrahydro-pyran-2-one