(3S,4R,5S)-6-(3R-butenyl)-4-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-one

Base Information

• Chemical Name: (3S,4R,5S)-6-(3R-butenyl)-4-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-one
• CAS No.: 286408-58-0
• Molecular Formula: C₁₈H₂₄O₄
• Molecular Weight: 304.386
• Mol file: 286408-58-0.mol

Synonyms:(3S,4R,5S)-6-(3R-butenyl)-4-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-one

Chemical Property of (3S,4R,5S)-6-(3R-butenyl)-4-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,5S)-6-(3R-butenyl)-4-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-one

There total 5 articles about (3S,4R,5S)-6-(3R-butenyl)-4-(4-methoxy-benzyloxy)-5-methyl-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: 78.0%

(2S,3S,4S)-2-(3R-butenyl)-3-methyl-4-[4-methoxy-benzyloxy]-cyclopentanone (286408-57-9) → (3S,4R,5S)-6-(3R-butenyl)-4-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-one (286408-58-0)

Guidance literature:

With bis-trimethylsilanyl peroxide; tin(IV) chloride; rac-diaminocyclohexane; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; for 48h;

DOI:10.1021/ol006003y

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (3S,4R,5S)-6-(3R-butenyl)-4-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-one (286408-58-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH; n-Bu₄NI / dimethylformamide; tetrahydrofuran / 0.67 h / 0 °C

1.2: 90 percent / dimethylformamide; tetrahydrofuran / 40 h / 20 °C

2.1: 98 percent / HCl / tetrahydrofuran; H₂O / 2 h / 40 °C

3.1: tetrahydrofuran; diethyl ether / 0.5 h / 25 °C

3.2: 82 percent / tetrahydrofuran; diethyl ether / 12 h / 50 °C

4.1: 81 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide / CH₂Cl₂ / 12 h / 20 °C

5.1: 78 percent / bis(trimethylsilyl) peroxide; 1,2-diaminocyclohexane; SnCl₄ / CH₂Cl₂; tetrahydrofuran / 48 h / 0 - 20 °C

With hydrogenchloride; tetrapropylammonium perruthennate; bis-trimethylsilanyl peroxide; tin(IV) chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; rac-diaminocyclohexane; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Reduction / 1.2: Addition / 2.1: Hydrolysis / 3.1: Addition / 3.2: Ring cleavage / 4.1: Oxidation / 5.1: Oxidation;

DOI:10.1021/ol006003y

Reference yield:

(1R,3RS,4S,5R,6S,7S)-4,6-dimethyl-7-[4-methoxy-benzyloxy]-2-oxabicyclo[3.3.0]-octane-3-ol (286408-55-7) → (3S,4R,5S)-6-(3R-butenyl)-4-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-one (286408-58-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran; diethyl ether / 0.5 h / 25 °C

1.2: 82 percent / tetrahydrofuran; diethyl ether / 12 h / 50 °C

2.1: 81 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide / CH₂Cl₂ / 12 h / 20 °C

3.1: 78 percent / bis(trimethylsilyl) peroxide; 1,2-diaminocyclohexane; SnCl₄ / CH₂Cl₂; tetrahydrofuran / 48 h / 0 - 20 °C

With tetrapropylammonium perruthennate; bis-trimethylsilanyl peroxide; tin(IV) chloride; rac-diaminocyclohexane; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Addition / 1.2: Ring cleavage / 2.1: Oxidation / 3.1: Oxidation;

DOI:10.1021/ol006003y

upstream raw materials:

(2S,3S,4S)-2-(3R-butenyl)-3-methyl-4-[4-methoxy-benzyloxy]-cyclopentanone

p-methoxybenzyl chloride

(1R,3RS,4S,5R,6S,7S)-4,6-dimethyl-7-[4-methoxy-benzyloxy]-2-oxabicyclo[3.3.0]-octane-3-ol

(1R,2S,3S,4S)-2-(3R-butenyl)-4-[4-methoxy-benzyloxy]-3-methyl-cyclopentanol