(-) (1'S,2'R)-2',3'-dihydro-abscisic acid

Base Information

• Chemical Name: (-) (1'S,2'R)-2',3'-dihydro-abscisic acid
• CAS No.: 130694-63-2
• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.337
• Mol file: 130694-63-2.mol

Synonyms:(-) (1'S,2'R)-2',3'-dihydro-abscisic acid

Chemical Property of (-) (1'S,2'R)-2',3'-dihydro-abscisic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-) (1'S,2'R)-2',3'-dihydro-abscisic acid

There total 17 articles about (-) (1'S,2'R)-2',3'-dihydro-abscisic acid 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%

(-)-(4R,5R)-methyl dihydroabscisate (130694-62-1) → (-) (1'S,2'R)-2',3'-dihydro-abscisic acid (130694-63-2)

Guidance literature:

With potassium hydroxide; In methanol; for 4h; Ambient temperature;

Reference yield:

(Z)-3-methylpent-2-en-4-ynol (6153-05-5,105-29-3) → (-) (1'S,2'R)-2',3'-dihydro-abscisic acid (130694-63-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / n-Bu-Li / hexane; tetrahydrofuran

2: Na-bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran / 1) 0 deg C, 1,5 h 2) r.t., 1 h

3: 60 percent / 1M HCl / acetone / 2 h / Ambient temperature

4: MnO₂ / acetone / 1 h / Ambient temperature

5: 70 percent / MnO₂, glacical acetic acid / 5 h / Ambient temperature

6: 78 percent / 2M KOH / methanol / 4 h / Ambient temperature

With hydrogenchloride; manganese(IV) oxide; potassium hydroxide; n-butyllithium; acetic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; hexane; acetone;

Reference yield:

(6R)-levodione (60046-49-3) → (-) (1'S,2'R)-2',3'-dihydro-abscisic acid (130694-63-2)

Guidance literature:

Multi-step reaction with 13 steps

1: 60 percent / tri-sec-butylborohydride / tetrahydrofuran / 0.5 h / -65 - -60 °C

2: 80 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

3: n-Bu-Li / THF, 1) -5 deg C, 30 min 2) -60 deg C to 0 deg C, 90 min

4: pyridine, 4-dimethylamino-pyridine / 1 h / Ambient temperature

5: glacical acetic acid, H₂O / 20 h / 70 °C

6: 84 percent / pyridinium dichromate / CH₂Cl₂ / 5 h / Ambient temperature

7: 87 percent / 5M NaOH / methanol / 1 h / Ambient temperature

8: 90 percent / pyridinium p-tosylate / benzene / 4 h / Heating

9: Na-bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran / 1) 0 deg C, 1,5 h 2) r.t., 1 h

10: 60 percent / 1M HCl / acetone / 2 h / Ambient temperature

11: MnO₂ / acetone / 1 h / Ambient temperature

12: 70 percent / MnO₂, glacical acetic acid / 5 h / Ambient temperature

13: 78 percent / 2M KOH / methanol / 4 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; dmap; manganese(IV) oxide; potassium hydroxide; sodium hydroxide; dipyridinium dichromate; n-butyllithium; water; pyridinium p-toluenesulfonate; Tri-sec-butylborhydrid-Anion; acetic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

upstream raw materials:

(2Z,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-2,4-pentadienoic acid

Abscisic acid

(-)-(4R,5R)-methyl dihydroabscisate

(Z)-3-methylpent-2-en-4-ynol

Downstream raw materials:

(1'S,2'R)-2',3'-dihydro-abscisic acid methyl ester

Refernces

• 1、 Arnone, Alberto,Cardillo, Rosanna,Nasini, Gianluca,Pava, Orso Vajna de. "Enantioselective Reduction of Racemic Abscisic Acid by Aspergillus niger Cultures". . p. 3061 - 3063. Retrieved 2007/10/02.