(4S)-4,5-Dihydro-4α-hydroxy-5β-methyl-3-[(E)-tetradecan-1-ylidene]furan-2(3H)-one

Base Information

• Chemical Name: (4S)-4,5-Dihydro-4α-hydroxy-5β-methyl-3-[(E)-tetradecan-1-ylidene]furan-2(3H)-one
• CAS No.: 38965-62-7
• Molecular Formula: C19H34O3
• Molecular Weight: 310.47146
• Mol file: 38965-62-7.mol

Synonyms:(4S,5R)-4-Hydroxy-5-methyl-3-tetradec-(E)-ylidene-dihydro-furan-2-one;Litsenolid C2;(-)-litsenolide C1;litsenolide C1;

Chemical Property of (4S)-4,5-Dihydro-4α-hydroxy-5β-methyl-3-[(E)-tetradecan-1-ylidene]furan-2(3H)-one

Chemical Property:

• PSA: 46.53000
• LogP: 4.92010

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (4S)-4,5-Dihydro-4α-hydroxy-5β-methyl-3-[(E)-tetradecan-1-ylidene]furan-2(3H)-one

There total 38 articles about (4S)-4,5-Dihydro-4α-hydroxy-5β-methyl-3-[(E)-tetradecan-1-ylidene]furan-2(3H)-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: 85.0%

(4S,5R)-4-methoxymethoxy-5-methyl-3-((E)-2-tetradecylidene)tetrahydro-2-furanone → (-)-litsenolide C1 (38965-62-7)

Guidance literature:

With hydrogenchloride; In methanol; at 60 ℃; for 0.5h;

DOI:10.1021/jo0002487

Reference yield: 83.0%

(3R,4R,5R)-3-Benzenesulfinyl-4-hydroxy-5-methyl-3-tetradecyl-dihydro-furan-2-one (111900-40-4) → (3S,4R)-2-tetradecanylidene-3-hydroxy-4-valerolactone (38965-61-6,38965-62-7,78340-32-6,78340-33-7,79056-37-4,79056-38-5,79980-81-7,111900-39-1,111900-41-5)

Guidance literature:

In benzene; at 80 ℃;

DOI:10.1246/cl.1987.875

Reference yield: 72.0%

4-O-(methoxybenzyl)litsenolide C2 (109519-18-8) → (-)-litsenolide C1 (38965-62-7)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; for 8h;

DOI:10.1039/P19870002681

upstream raw materials:

4-O-(methoxybenzyl)litsenolide C₂

2-tetradecynal

(n-tetradecyl)triphenylphosphonium bromide

methoxy 5-deoxy-3-O-(p-methoxybenzyl)-α,β-erythro-pentofuranoside

Refernces

• 1、 Wood, William W.,Watson, Graham M.. "The Total Synthesis of (-)-Litsenolides C-1 and C-2". . p. 2681 - 2688. Retrieved 2007/10/02.
• 2、 Wood, William W.,Watson, Graham M.. "The Total Synthesis of Litsenolides C1 and C2". . p. 1599 - 1600. Retrieved 2007/10/02.