9,12,15-cis-Octadecatrienoic acid → N-(cis-9,12,15-Octadecatrienoyl)-O-phospho-L-Threonine

Participants

Role	Name	HCID	Charge
Reactant	9,12,15-cis-Octadecatrienoic acid	HCID 445640	—
Reactant	Methyl L-threoninate hydrochloride	HCID 2734893	—
Reactant	N-(cis-5,8,11,14-Eicosatetraenoyl)-O-Phospho-L-Serine	HCID 86583929	—
Product	N-(cis-9,12,15-Octadecatrienoyl)-O-phospho-L-Threonine	HCID 86583937	—

Reaction Steps

This compound was prepared as described above for (6), using 0.5 mmol (139 mg) of cis-9,12,15-octadecatrienoic acid and 1 mmol (170 mg) of L-threonine methyl ester hydrochloride; yield 85 mg (37%); Rf 0.05-0.10 (system B); 1H-NMR (CD3SOCD3, 200 MHz) δ0.9-1.0 (t, 3H, ω-CH3); 1.3-1.5 (m, 13H, 5CH2 and CH3CHOP); 2.0-2.2 (m, 6H, CH2CO and 2CH2CH═CH); 2.7-2.9 (br s, 4H, 2HC═CH—CH2—CH═CH); 4.1-4.3 (m, 2H, 2CH); 5.2-5.4 (br s, 6H, 3HC═CH); 8.2-8.4 (m, 3H, NH and 2POH)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06274747B1
Source dataset	uspto-grants-2001_08
ORD ID	ord-77364808adbc41cf82af204f72d8d8be
Source note	uspto-grants-2001_08