(+)-(5S)-hydroxy-(2E)-hexenal

Base Information

• Chemical Name: (+)-(5S)-hydroxy-(2E)-hexenal
• CAS No.: 93382-53-7
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.144
• Mol file: 93382-53-7.mol

Synonyms:(+)-(5S)-hydroxy-(2E)-hexenal

Chemical Property of (+)-(5S)-hydroxy-(2E)-hexenal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(5S)-hydroxy-(2E)-hexenal

There total 1 articles about (+)-(5S)-hydroxy-(2E)-hexenal 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:

acetaldehyde (75-07-0,9002-91-9) → trans,trans-2,4-Hexadienal (142-83-6,4488-48-6) + (-)-(5R)-hydroxy-(2E)-hexenal (69830-85-9) + (+)-(5S)-hydroxy-(2E)-hexenal (93382-53-7)

Guidance literature:

With L-proline; In tetrahydrofuran; at 4 ℃; for 14h; Title compound not separated from byproducts;

DOI:10.1021/jo015881m

Reference yield:

(+)-(5S)-hydroxy-(2E)-hexenal (93382-53-7) → ethyl 2-{(R)-2-(tert-butyldimethylsilyloxy)-3-[(2S,6S)-6-methyl-5,6-dihydro-2H-pyran-2-yl]propyl}-4,6-dimethoxybenzoate (1454318-22-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: AD-mix-α / tert-butyl alcohol; water / 0 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

2.2: tosylimidazole / 0.5 h / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / Inert atmosphere

3.2: 1 h / 0 °C / Inert atmosphere

4.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

5.1: N,N-dimethyl-aniline / neat (no solvent) / 48 h / 200 °C / Inert atmosphere; Sealed tube

With 2,6-dimethylpyridine; n-butyllithium; AD-mix-α; sodium hydride; N,N-dimethyl-aniline; In tetrahydrofuran; hexane; dichloromethane; water; mineral oil; tert-butyl alcohol; 1.1: |Sharpless Dihydroxylation / 5.1: |Alder-Rickert Cycloaddition;

DOI:10.1002/ejoc.201300053

Reference yield:

(+)-(5S)-hydroxy-(2E)-hexenal (93382-53-7) → tert-butyl (S)-7-{2-[3,5-bis(benzyloxy)phenyl]acetoxy}octoanoate

Guidance literature:

Multi-step reaction with 4 steps

1: dichloromethane / 20 °C / Inert atmosphere

2: hydrogen; palladium on activated charcoal / dichloromethane / 20 °C / 760.05 Torr / Inert atmosphere

3: pyridine; 2-Bromoacetyl bromide / dichloromethane / 0 - 20 °C / Inert atmosphere

4: palladium diacetate; potassium phosphate; tris-(o-tolyl)phosphine / tetrahydrofuran; water / 24 h / Glovebox

With pyridine; potassium phosphate; palladium on activated charcoal; hydrogen; palladium diacetate; 2-Bromoacetyl bromide; tris-(o-tolyl)phosphine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/ejoc.201500287

upstream raw materials:

acetaldehyde

Downstream raw materials:

ethyl 2-{(R)-2-(tert-butyldimethylsilyloxy)-3-[(2S,6S)-6-methyl-5,6-dihydro-2H-pyran-2-yl]propyl}-4,6-dimethoxybenzoate

(7S)-7-{2-[3,5-bis(benzyloxy)phenyl]acetoxy}octanoic acid

(S)-di-O-benzylcurvularin

curvularin