D-threo-Pentonic acid, 2,3-dideoxy-3-(1-methylethyl)-, gamma-lactone (9CI)

Base Information

• Chemical Name: D-threo-Pentonic acid, 2,3-dideoxy-3-(1-methylethyl)-, gamma-lactone (9CI)
• CAS No.: 189758-62-1
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.197
• Mol file: 189758-62-1.mol

Synonyms:D-threo-Pentonic acid, 2,3-dideoxy-3-(1-methylethyl)-, gamma-lactone (9CI)

Chemical Property of D-threo-Pentonic acid, 2,3-dideoxy-3-(1-methylethyl)-, gamma-lactone (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of D-threo-Pentonic acid, 2,3-dideoxy-3-(1-methylethyl)-, gamma-lactone (9CI)

There total 12 articles about D-threo-Pentonic acid, 2,3-dideoxy-3-(1-methylethyl)-, gamma-lactone (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: 66.0%

(4R,5S)-4-Isopropyl-5-trityloxymethyl-dihydro-furan-2-one (156847-90-4) → 3-C-isopropyl-2,3-dideoxy-D-erythro-pentono-1,4-lactone (156847-97-1,189758-62-1)

Guidance literature:

With hydrogenchloride; In methanol; dichloromethane; for 1h; Ambient temperature;

DOI:10.1016/0008-6215(94)80067-7

Reference yield: 55.0%

(S)-4-Isopropyl-5-((E)-pent-1-enyl)-dihydro-furan-2-one (848401-35-4) → (4R,3S)-4,5-dihydroxy-3-(1-methylethyl)pentanoic acid γ-lactone (189758-62-1) + (4S,5R)-5-Hydroxymethyl-4-isopropyl-dihydro-furan-2-one

Guidance literature:

(S)-4-Isopropyl-5-((E)-pent-1-enyl)-dihydro-furan-2-one; With oxygen; ozone; In methanol; at -78 ℃; for 0.166667h;

With dimethylsulfide; at -78 - 0 ℃; for 1h;

With sodium tetrahydroborate; at 0 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2004.12.132

Reference yield:

methyl (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate (81703-94-8) → 3-C-isopropyl-2,3-dideoxy-D-erythro-pentono-1,4-lactone (156847-97-1,189758-62-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / CuI; Zn / aq. ethanol / 3 h / 20 °C / ultrasonic irradiation

2: aq. HCl / methanol / 1 h

With hydrogenchloride; copper(l) iodide; zinc; In methanol; ethanol;

DOI:10.1002/chem.200304790

upstream raw materials:

(4R,5S)-4-Isopropyl-5-trityloxymethyl-dihydro-furan-2-one

methyl (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate

(S)-4-Isopropyl-5-((E)-pent-1-enyl)-dihydro-furan-2-one

(S)-3-Formyl-4-methyl-pentanoic acid methyl ester