ChemicalBook CAS DataBase List lycophyll

lycophyll synthesis

8synthesis methods

Product Name:lycophyll
CAS Number:19891-75-9
Molecular formula:C40H56O2
Molecular Weight:568.87

ψ,ψ-Carotene-16,16'-dioic acid, 16,16'-dimethyl ester, (1-trans,1'-trans)-

40772-87-0
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19891-75-9
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Yield:19891-75-9 38%

Reaction Conditions:

Stage #1: dimethyl Ψ,Ψ-carotene-16,16'-dioatewith diisobutylaluminium hydride in tetrahydrofuran;toluene at 0 - 20; for 1 h;
Stage #2: with sodium hydroxide;water in tetrahydrofuran;toluene; for 0.5 h;

Steps:

15

Example 15 Preparation of ψ,ψ-Carotene-16,16'-diol (2H) To a solution of dimethyl ester 218a (1.14 g, 1.83 mmol) in anhydrous tetrahydrofuran (100 mL) at 0° C. was added DIBAL (20% by wt. in toluene) (9.13 μL, 11.0 mmol) via syringe. The mixture was warmed to room temperature and stirred for one hour. The reaction was quenched by the sequential addition of H₂O (440 μL), 15% aqueous NaOH (440 μL), and H₂O (1.10 mL). The resulting mixture was stirred for 30 minutes and then dried over anhydrous MgSO₄. After filtration and removal of solvent in vacuo, the resulting crude diol 2H (0.39 g, 38%) was used in the next step without further purification. ¹H NMR (500 MHz, CDCl₃) δ: 6.63 (d of d, J=15.0 Hz, J=11.5 Hz, 2H, H11, H11'), 6.63 (d, J=11.0 Hz, 2H, H15, H15'), 6.48 (d of d, J=15.0 Hz, J=11.0 Hz, 2H, H7, H7'), 6.36 (d, J=15.0 Hz, 2H, H12, H12'), 6.25 (d, J=15.0 Hz, 2H, H8, H8'), 6.19 (d, J=11.5 Hz, 2H, H10, H10'), 5.95 (d, J=11.0 Hz, 2H, H6, H6'), 5.40 (t of q, J=6.50 Hz, J=1.50 Hz, 2H, H2, H2'), 4.00 (s, 4H, -CH₂O-), 2.19 (t, J=Hz, 4H, -CH₂-), 2.16 (t, J=Hz, 4H, -CH₂-), LC/MS (APCI): m/z 569 [M+H]⁺.

References:

US2008/221377,2008,A1 Location in patent:Page/Page column 40; 20

105-87-3 Synthesis