(+/-)-β,β-Carotin-cis,cis-3,4,3',4'-tetrol

Base Information

• Chemical Name: (+/-)-β,β-Carotin-cis,cis-3,4,3',4'-tetrol
• CAS No.: 130930-16-4
• Molecular Formula: C₄₀H₅₆O₄
• Molecular Weight: 600.882
• Mol file: 130930-16-4.mol

Synonyms:

Chemical Property of (+/-)-β,β-Carotin-cis,cis-3,4,3',4'-tetrol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-β,β-Carotin-cis,cis-3,4,3',4'-tetrol

There total 31 articles about (+/-)-β,β-Carotin-cis,cis-3,4,3',4'-tetrol 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: 48.0%

(3S,4S,3'S,4'S)-3,4,3',4'-Tetrakis<(trimethylsilyl)oxy>-β,β-carotin (55497-61-5,130856-68-7,130930-15-3) → (3S,4S,3'S,4'S)-Crustaxanthin (6094-35-5,28082-20-4,55222-10-1,106037-12-1,130856-69-8,130930-13-1,130930-16-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1002/hlca.19900730426

Reference yield:

(E)-4-(1',6'-Epoxy-2',2',6'-trimethyl-4'-cyclohexen-1'-yl)-3-buten-2-on (30981-78-3,54685-98-2,75222-70-7,80924-22-7) → (+/-)-β,β-Carotin-cis,cis-3,4,3',4'-tetrol (6094-35-5,28082-20-4,55222-10-1,106037-12-1,130856-69-8,130930-13-1,130930-16-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 52 percent / conc. H₂SO₄ / acetic acid; diethyl ether / 2 h / 0 °C

2: 6.6 g / KOH / methanol / 2 h / Ambient temperature

3: 3.16 g / TsOH / CH₂Cl₂ / 4 h

4: 1.2 g

5: 0.80 g / DIBAH / hexane; diethyl ether / 0 °C

6: 295 g / MnO₂ / ethyl acetate / 1.5 h

7: 52 mg / aq. AcOH / Ambient temperature

8: 94 percent / pyridine / 4-(Dimethylamino)pyridin

9: 2 percent / NaOMe / methanol

With pyridine; manganese(IV) oxide; potassium hydroxide; sodium methylate; diisobutylaluminium hydride; acetic acid; dmap; sulfuric acid; toluene-4-sulfonic acid; In methanol; diethyl ether; hexane; dichloromethane; acetic acid; ethyl acetate;

DOI:10.1002/hlca.19900730426

Reference yield:

(+)-(S)-5-(1'-Hydroxy-2',6',6'-trimethyl-4'-oxocyclohex-2'-enyl)-3-methylpenta-2,4-diennitril (130856-58-5) → (3S,4S,3'S,4'S)-Crustaxanthin (6094-35-5,28082-20-4,55222-10-1,106037-12-1,130856-69-8,130930-13-1,130930-16-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 3.94 g / 9-BBN / tetrahydrofuran / 0 °C

2: 88 percent / pyridine

3: 4.20 g / conc. H₂SO₄ / acetic acid / 0.25 h

4: 31 percent / K₂CO₃ / methanol; H₂O / Ambient temperature

5: 98 percent / hexamethyl disilazane / pyridine / Ambient temperature

6: 1.50 g / DIBAH / hexane; diethyl ether / -10 °C

7: 1.) BuLi / 1.) - 78 deg C, THF/DMPU, hexane; 2.) RT, THF

8: 27 percent / 2,23 Lindlar-Katalysator / ethyl acetate

9: 48 percent / (Bu)4NF / tetrahydrofuran

With pyridine; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; Pd/CaCO₃; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; sulfuric acid; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; water; acetic acid; ethyl acetate;

DOI:10.1002/hlca.19900730426

upstream raw materials:

(3S,4S,3'S,4'S)-3,4,3',4'-Tetrakis<(trimethylsilyl)oxy>-β,β-carotin

(+)-(S)-5-(1'-Hydroxy-2',6',6'-trimethyl-4'-oxocyclohex-2'-enyl)-3-methylpenta-2,4-diennitril

(-)-(1'S,2'R)-5-(1',2'-Epoxy-4',4'-(ethylendioxy)-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-diennitril

(1'RS,6'S)-Essigsaeure-<6'-acetoxy-3'-(4''-cyano-3''-methylbuta-1'',3''-dienyl)-2',4',4'-trimethylcyclohex-2'-enyl>ester