2H-Pyran-2-one,tetrahydro-4-hydroxy-5-methyl-6-(1-methylethyl)-,(4S,5S,6R)-(9CI)

Base Information

• Chemical Name: 2H-Pyran-2-one,tetrahydro-4-hydroxy-5-methyl-6-(1-methylethyl)-,(4S,5S,6R)-(9CI)
• CAS No.: 224580-59-0
• Molecular Formula: C₉H₁₆O₃
• Molecular Weight: 172.224
• Mol file: 224580-59-0.mol

Synonyms:2H-Pyran-2-one,tetrahydro-4-hydroxy-5-methyl-6-(1-methylethyl)-,(4S,5S,6R)-(9CI)

Chemical Property of 2H-Pyran-2-one,tetrahydro-4-hydroxy-5-methyl-6-(1-methylethyl)-,(4S,5S,6R)-(9CI)

Chemical Property:

• PSA: 46.53000
• LogP: 0.95490

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2H-Pyran-2-one,tetrahydro-4-hydroxy-5-methyl-6-(1-methylethyl)-,(4S,5S,6R)-(9CI)

There total 8 articles about 2H-Pyran-2-one,tetrahydro-4-hydroxy-5-methyl-6-(1-methylethyl)-,(4S,5S,6R)-(9CI) 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:

(4S,5R)-5-hydroxy-4,6-dimethyl-3-oxoheptanoic acid methyl ester (795279-41-3) → (+)-prelactone B (147659-07-2,616207-71-7,518348-13-5) + (3S,4S,5R)-3-Hydroxy-4,6-dimethylheptanoic acid δ-lactone (224580-59-0,616207-71-7,518348-13-5)

Guidance literature:

(4S,5R)-5-hydroxy-4,6-dimethyl-3-oxoheptanoic acid methyl ester; With sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; at -78 - 20 ℃;

With hydrogenchloride; acetic acid; In tetrahydrofuran; at 20 ℃; Further stages.;

DOI:10.1016/j.tet.2004.07.044

Reference yield:

tert-Butyl (3SR,4S,5R)-5-<(tert-butyldimethylsilyl)oxy>-3-hydroxy-4,6-dimethylheptanoate (224580-63-6) → (+)-prelactone B (147659-07-2,616207-71-7,518348-13-5) + (3S,4S,5R)-3-Hydroxy-4,6-dimethylheptanoic acid δ-lactone (224580-59-0,616207-71-7,518348-13-5)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; for 168h; Yields of byproduct given; Ambient temperature;

DOI:10.1055/s-1999-3421

Reference yield:

(2R,3R)-2-(5-methoxycyclohexa-1,4-dienyl)-4-methylpentan-2-ol (795279-40-2) → (3S,4S,5R)-3-Hydroxy-4,6-dimethylheptanoic acid δ-lactone (224580-59-0,616207-71-7,518348-13-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: O₃; pyridine / methanol; CH₂Cl₂ / -78 °C

1.2: PPh₃ / methanol; CH₂Cl₂ / 1 h / 20 °C

2.1: NaBH(OAc)3; AcOH / tetrahydrofuran / -78 - 20 °C

2.2: aq. HCl; AcOH / tetrahydrofuran / 20 °C

With pyridine; sodium tris(acetoxy)borohydride; ozone; acetic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.tet.2004.07.044

upstream raw materials:

tert-Butyl (3SR,4S,5R)-5-<(tert-butyldimethylsilyl)oxy>-3-hydroxy-4,6-dimethylheptanoate

(2R,3R,4S)-4-Hydroxy-2-isopropyl-3-methyl-cyclopentanone

(4S,5R)-5-hydroxy-4,6-dimethyl-3-oxoheptanoic acid methyl ester

(2R,3R)-2-(5-methoxycyclohexa-1,4-dienyl)-4-methylpentan-2-ol

Downstream raw materials:

(+)-5(S)-methyl-6(R)-isopropyl-5,6-dihydro-pyran-2-one